fix: resolve 5 invoice/payment issues from user feedback

- Replace misleading 'sent' status with 'pending' (no email capability)
- Show assessment group name instead of raw 'regular_assessment' type
- Add owner last name to invoice table
- Fix payment creation Internal Server Error (PostgreSQL $2 type cast)
- Add edit/delete capability for payment records with invoice recalc

Co-Authored-By: Claude Opus 4.6 <noreply@anthropic.com>

backend/src/database/tenant-schema.service.ts

@@ -112,6 +112,8 @@ export class TenantSchemaService {
         special_assessment DECIMAL(10,2) DEFAULT 0.00,
         unit_count INTEGER DEFAULT 0,
         frequency VARCHAR(20) DEFAULT 'monthly' CHECK (frequency IN ('monthly', 'quarterly', 'annual')),
+        due_months INTEGER[] DEFAULT '{1,2,3,4,5,6,7,8,9,10,11,12}',
+        due_day INTEGER DEFAULT 1,
         is_default BOOLEAN DEFAULT FALSE,
         is_active BOOLEAN DEFAULT TRUE,
         created_at TIMESTAMPTZ DEFAULT NOW(),
@@ -155,8 +157,11 @@ export class TenantSchemaService {
         amount DECIMAL(10,2) NOT NULL,
         amount_paid DECIMAL(10,2) DEFAULT 0.00,
         status VARCHAR(20) DEFAULT 'draft' CHECK (status IN (
-          'draft', 'sent', 'paid', 'partial', 'overdue', 'void', 'written_off'
+          'draft', 'pending', 'sent', 'paid', 'partial', 'overdue', 'void', 'written_off'
         )),
+        period_start DATE,
+        period_end DATE,
+        assessment_group_id UUID REFERENCES "${s}".assessment_groups(id),
         journal_entry_id UUID REFERENCES "${s}".journal_entries(id),
         sent_at TIMESTAMPTZ,
         paid_at TIMESTAMPTZ,
@@ -325,8 +330,6 @@ export class TenantSchemaService {
         risk_notes JSONB,
         requested_by UUID,
         response_time_ms INTEGER,
-        status VARCHAR(20) DEFAULT 'complete',
-        error_message TEXT,
         created_at TIMESTAMPTZ DEFAULT NOW()
       )`,
 

backend/src/modules/assessment-groups/assessment-groups.service.ts

@@ -1,6 +1,12 @@
-import { Injectable, NotFoundException } from '@nestjs/common';
+import { Injectable, NotFoundException, BadRequestException } from '@nestjs/common';
 import { TenantService } from '../../database/tenant.service';
 
+const DEFAULT_DUE_MONTHS: Record<string, number[]> = {
+  monthly: [1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12],
+  quarterly: [1, 4, 7, 10],
+  annual: [1],
+};
+
 @Injectable()
 export class AssessmentGroupsService {
   constructor(private tenant: TenantService) {}
@@ -42,6 +48,33 @@ export class AssessmentGroupsService {
     return rows.length ? rows[0] : null;
   }
 
+  private validateDueMonths(frequency: string, dueMonths: number[]) {
+    if (!dueMonths || !dueMonths.length) {
+      throw new BadRequestException('Due months are required');
+    }
+    // Validate all values are 1-12
+    if (dueMonths.some((m) => m < 1 || m > 12 || !Number.isInteger(m))) {
+      throw new BadRequestException('Due months must be integers between 1 and 12');
+    }
+    switch (frequency) {
+      case 'monthly':
+        if (dueMonths.length !== 12) {
+          throw new BadRequestException('Monthly frequency must include all 12 months');
+        }
+        break;
+      case 'quarterly':
+        if (dueMonths.length !== 4) {
+          throw new BadRequestException('Quarterly frequency must have exactly 4 due months');
+        }
+        break;
+      case 'annual':
+        if (dueMonths.length !== 1) {
+          throw new BadRequestException('Annual frequency must have exactly 1 due month');
+        }
+        break;
+    }
+  }
+
   async create(dto: any) {
     const existingGroups = await this.tenant.query('SELECT COUNT(*) as cnt FROM assessment_groups');
     const isFirstGroup = parseInt(existingGroups[0].cnt) === 0;
@@ -51,17 +84,23 @@ export class AssessmentGroupsService {
       await this.tenant.query('UPDATE assessment_groups SET is_default = false WHERE is_default = true');
     }
 
+    const frequency = dto.frequency || 'monthly';
+    const dueMonths = dto.dueMonths || DEFAULT_DUE_MONTHS[frequency] || DEFAULT_DUE_MONTHS.monthly;
+    const dueDay = Math.min(Math.max(dto.dueDay || 1, 1), 28);
+
+    this.validateDueMonths(frequency, dueMonths);
+
     const rows = await this.tenant.query(
-      `INSERT INTO assessment_groups (name, description, regular_assessment, special_assessment, unit_count, frequency, is_default)
-       VALUES ($1, $2, $3, $4, $5, $6, $7) RETURNING *`,
+      `INSERT INTO assessment_groups (name, description, regular_assessment, special_assessment, unit_count, frequency, due_months, due_day, is_default)
+       VALUES ($1, $2, $3, $4, $5, $6, $7, $8, $9) RETURNING *`,
       [dto.name, dto.description || null, dto.regularAssessment || 0, dto.specialAssessment || 0,
-       dto.unitCount || 0, dto.frequency || 'monthly', shouldBeDefault],
+       dto.unitCount || 0, frequency, dueMonths, dueDay, shouldBeDefault],
     );
     return rows[0];
   }
 
   async update(id: string, dto: any) {
-    await this.findOne(id);
+    const existing = await this.findOne(id);
 
     if (dto.isDefault === true) {
       await this.tenant.query('UPDATE assessment_groups SET is_default = false WHERE is_default = true');
@@ -80,6 +119,24 @@ export class AssessmentGroupsService {
     if (dto.frequency !== undefined) { sets.push(`frequency = $${idx++}`); params.push(dto.frequency); }
     if (dto.isDefault !== undefined) { sets.push(`is_default = $${idx++}`); params.push(dto.isDefault); }
 
+    // Handle due_months: if frequency changed and no explicit dueMonths, auto-populate defaults
+    const effectiveFrequency = dto.frequency || existing.frequency;
+    if (dto.dueMonths !== undefined) {
+      this.validateDueMonths(effectiveFrequency, dto.dueMonths);
+      sets.push(`due_months = $${idx++}`);
+      params.push(dto.dueMonths);
+    } else if (dto.frequency !== undefined && dto.frequency !== existing.frequency) {
+      // Frequency changed, auto-populate due_months
+      const newDueMonths = DEFAULT_DUE_MONTHS[dto.frequency] || DEFAULT_DUE_MONTHS.monthly;
+      sets.push(`due_months = $${idx++}`);
+      params.push(newDueMonths);
+    }
+
+    if (dto.dueDay !== undefined) {
+      sets.push(`due_day = $${idx++}`);
+      params.push(Math.min(Math.max(dto.dueDay, 1), 28));
+    }
+
     if (!sets.length) return this.findOne(id);
 
     sets.push('updated_at = NOW()');

backend/src/modules/health-scores/health-scores.controller.ts

@@ -1,4 +1,4 @@
-import { Controller, Get, Post, UseGuards, Req, Logger } from '@nestjs/common';
+import { Controller, Get, Post, UseGuards, Req } from '@nestjs/common';
 import { ApiTags, ApiBearerAuth, ApiOperation } from '@nestjs/swagger';
 import { JwtAuthGuard } from '../auth/guards/jwt-auth.guard';
 import { AllowViewer } from '../../common/decorators/allow-viewer.decorator';
@@ -9,8 +9,6 @@ import { HealthScoresService } from './health-scores.service';
 @ApiBearerAuth()
 @UseGuards(JwtAuthGuard)
 export class HealthScoresController {
-  private readonly logger = new Logger(HealthScoresController.name);
-
   constructor(private service: HealthScoresService) {}
 
   @Get('latest')
@@ -21,56 +19,32 @@ export class HealthScoresController {
   }
 
   @Post('calculate')
-  @ApiOperation({ summary: 'Trigger both health score recalculations (async — returns immediately)' })
+  @ApiOperation({ summary: 'Trigger both health score recalculations (used by scheduler)' })
   @AllowViewer()
   async calculate(@Req() req: any) {
     const schema = req.user?.orgSchema;
-
-    // Fire-and-forget — background processing saves results to DB
-    Promise.all([
+    const [operating, reserve] = await Promise.all([
       this.service.calculateScore(schema, 'operating'),
       this.service.calculateScore(schema, 'reserve'),
-    ]).catch((err) => {
-      this.logger.error(`Background health score calculation failed: ${err.message}`);
-    });
-
-    return {
-      status: 'processing',
-      message: 'Health score calculations started. Results will appear when ready.',
-    };
+    ]);
+    return { operating, reserve };
   }
 
   @Post('calculate/operating')
-  @ApiOperation({ summary: 'Trigger operating fund health score recalculation (async)' })
+  @ApiOperation({ summary: 'Recalculate operating fund health score only' })
   @AllowViewer()
   async calculateOperating(@Req() req: any) {
     const schema = req.user?.orgSchema;
-
-    // Fire-and-forget
-    this.service.calculateScore(schema, 'operating').catch((err) => {
-      this.logger.error(`Background operating score failed: ${err.message}`);
-    });
-
-    return {
-      status: 'processing',
-      message: 'Operating fund health score calculation started.',
-    };
+    const operating = await this.service.calculateScore(schema, 'operating');
+    return { operating };
   }
 
   @Post('calculate/reserve')
-  @ApiOperation({ summary: 'Trigger reserve fund health score recalculation (async)' })
+  @ApiOperation({ summary: 'Recalculate reserve fund health score only' })
   @AllowViewer()
   async calculateReserve(@Req() req: any) {
     const schema = req.user?.orgSchema;
-
-    // Fire-and-forget
-    this.service.calculateScore(schema, 'reserve').catch((err) => {
-      this.logger.error(`Background reserve score failed: ${err.message}`);
-    });
-
-    return {
-      status: 'processing',
-      message: 'Reserve fund health score calculation started.',
-    };
+    const reserve = await this.service.calculateScore(schema, 'reserve');
+    return { reserve };
   }
 }

backend/src/modules/health-scores/health-scores.service.ts

@@ -1115,7 +1115,7 @@ Projected Year-End Total (Cash + Investments): $${data.projectedYearEndTotal.toF
             'Content-Type': 'application/json',
             'Content-Length': Buffer.byteLength(bodyString, 'utf-8'),
           },
-          timeout: 600000, // 10 minute timeout
+          timeout: 120000,
         };
 
         const req = https.request(options, (res) => {
@@ -1129,7 +1129,7 @@ Projected Year-End Total (Cash + Investments): $${data.projectedYearEndTotal.toF
         req.on('error', (err) => reject(err));
         req.on('timeout', () => {
           req.destroy();
-          reject(new Error('Request timed out after 600s'));
+          reject(new Error('Request timed out after 120s'));
         });
 
         req.write(bodyString);

backend/src/modules/investment-planning/investment-planning.controller.ts

@@ -36,9 +36,9 @@ export class InvestmentPlanningController {
   }
 
   @Post('recommendations')
-  @ApiOperation({ summary: 'Trigger AI-powered investment recommendations (async — returns immediately)' })
+  @ApiOperation({ summary: 'Get AI-powered investment recommendations' })
   @AllowViewer()
-  triggerRecommendations(@Req() req: any) {
-    return this.service.triggerAIRecommendations(req.user?.sub, req.user?.orgId);
+  getRecommendations(@Req() req: any) {
+    return this.service.getAIRecommendations(req.user?.sub, req.user?.orgId);
   }
 }

backend/src/modules/investment-planning/investment-planning.service.ts

@@ -65,9 +65,6 @@ export interface SavedRecommendation {
   risk_notes: string[];
   response_time_ms: number;
   created_at: string;
-  status: 'processing' | 'complete' | 'error';
-  last_failed: boolean;
-  error_message?: string;
 }
 
 @Injectable()
@@ -199,33 +196,14 @@ export class InvestmentPlanningService {
     return rates.cd;
   }
 
-  /**
-   * Ensure the status/error_message columns exist (for tenants created before this migration).
-   */
-  private async ensureStatusColumn(): Promise<void> {
-    try {
-      await this.tenant.query(
-        `ALTER TABLE ai_recommendations ADD COLUMN IF NOT EXISTS status VARCHAR(20) DEFAULT 'complete'`,
-      );
-      await this.tenant.query(
-        `ALTER TABLE ai_recommendations ADD COLUMN IF NOT EXISTS error_message TEXT`,
-      );
-    } catch {
-      // Ignore — column may already exist or table may not exist
-    }
-  }
-
   /**
    * Get the latest saved AI recommendation for this tenant.
-   * Returns status and last_failed flag for UI state management.
    */
   async getSavedRecommendation(): Promise<SavedRecommendation | null> {
     try {
-      await this.ensureStatusColumn();
-
       const rows = await this.tenant.query(
         `SELECT id, recommendations_json, overall_assessment, risk_notes,
-                response_time_ms, status, error_message, created_at
+                response_time_ms, created_at
          FROM ai_recommendations
          ORDER BY created_at DESC
          LIMIT 1`,
@@ -234,64 +212,6 @@ export class InvestmentPlanningService {
       if (!rows || rows.length === 0) return null;
 
       const row = rows[0];
-      const status = row.status || 'complete';
-
-      // If still processing, return processing status
-      if (status === 'processing') {
-        return {
-          id: row.id,
-          recommendations: [],
-          overall_assessment: '',
-          risk_notes: [],
-          response_time_ms: 0,
-          created_at: row.created_at,
-          status: 'processing',
-          last_failed: false,
-        };
-      }
-
-      // If latest attempt failed, return the last successful result with last_failed flag
-      if (status === 'error') {
-        const lastGood = await this.tenant.query(
-          `SELECT id, recommendations_json, overall_assessment, risk_notes,
-                  response_time_ms, created_at
-           FROM ai_recommendations
-           WHERE status = 'complete'
-           ORDER BY created_at DESC
-           LIMIT 1`,
-        );
-
-        if (lastGood?.length) {
-          const goodRow = lastGood[0];
-          const recData = goodRow.recommendations_json || {};
-          return {
-            id: goodRow.id,
-            recommendations: recData.recommendations || [],
-            overall_assessment: goodRow.overall_assessment || recData.overall_assessment || '',
-            risk_notes: goodRow.risk_notes || recData.risk_notes || [],
-            response_time_ms: goodRow.response_time_ms || 0,
-            created_at: goodRow.created_at,
-            status: 'complete',
-            last_failed: true,
-            error_message: row.error_message,
-          };
-        }
-
-        // No previous good result — return error state
-        return {
-          id: row.id,
-          recommendations: [],
-          overall_assessment: row.error_message || 'AI analysis failed. Please try again.',
-          risk_notes: [],
-          response_time_ms: 0,
-          created_at: row.created_at,
-          status: 'error',
-          last_failed: true,
-          error_message: row.error_message,
-        };
-      }
-
-      // Complete — return the data normally
       const recData = row.recommendations_json || {};
       return {
         id: row.id,
@@ -300,8 +220,6 @@ export class InvestmentPlanningService {
         risk_notes: row.risk_notes || recData.risk_notes || [],
         response_time_ms: row.response_time_ms || 0,
         created_at: row.created_at,
-        status: 'complete',
-        last_failed: false,
       };
     } catch (err: any) {
       // Table might not exist yet (pre-migration tenants)
@@ -310,153 +228,15 @@ export class InvestmentPlanningService {
     }
   }
 
-  /**
-   * Save a 'processing' placeholder record and return its ID.
-   */
-  private async saveProcessingRecord(userId?: string): Promise<string> {
-    await this.ensureStatusColumn();
-    const rows = await this.tenant.query(
-      `INSERT INTO ai_recommendations
-       (recommendations_json, overall_assessment, risk_notes, requested_by, status)
-       VALUES ('{}', '', '[]', $1, 'processing')
-       RETURNING id`,
-      [userId || null],
-    );
-    return rows[0].id;
-  }
-
-  /**
-   * Update a processing record with completed results.
-   */
-  private async updateRecommendationComplete(
-    jobId: string,
-    aiResponse: AIResponse,
-    userId: string | undefined,
-    elapsed: number,
-  ): Promise<void> {
-    try {
-      await this.tenant.query(
-        `UPDATE ai_recommendations
-         SET recommendations_json = $1,
-             overall_assessment = $2,
-             risk_notes = $3,
-             response_time_ms = $4,
-             status = 'complete'
-         WHERE id = $5`,
-        [
-          JSON.stringify(aiResponse),
-          aiResponse.overall_assessment || '',
-          JSON.stringify(aiResponse.risk_notes || []),
-          elapsed,
-          jobId,
-        ],
-      );
-    } catch (err: any) {
-      this.logger.warn(`Could not update recommendation ${jobId}: ${err.message}`);
-    }
-  }
-
-  /**
-   * Update a processing record with error status.
-   */
-  private async updateRecommendationError(jobId: string, errorMessage: string): Promise<void> {
-    try {
-      await this.tenant.query(
-        `UPDATE ai_recommendations
-         SET status = 'error',
-             error_message = $1
-         WHERE id = $2`,
-        [errorMessage, jobId],
-      );
-    } catch (err: any) {
-      this.logger.warn(`Could not update recommendation error ${jobId}: ${err.message}`);
-    }
-  }
-
-  /**
-   * Trigger AI recommendations asynchronously.
-   * Saves a 'processing' record, starts the AI work in the background, and returns immediately.
-   * The TenantService instance remains alive via closure reference for the duration of the background work.
-   */
-  async triggerAIRecommendations(userId?: string, orgId?: string): Promise<{ status: string; message: string }> {
-    const jobId = await this.saveProcessingRecord(userId);
-    this.logger.log(`AI recommendation triggered (job ${jobId}), starting background processing...`);
-
-    // Fire-and-forget — the Promise keeps this service instance (and TenantService) alive
-    this.runBackgroundRecommendations(jobId, userId, orgId).catch((err) => {
-      this.logger.error(`Background AI recommendation failed (job ${jobId}): ${err.message}`);
-    });
-
-    return {
-      status: 'processing',
-      message: 'AI analysis has been started. You can navigate away safely — results will appear when ready.',
-    };
-  }
-
-  /**
-   * Run the full AI recommendation pipeline in the background.
-   */
-  private async runBackgroundRecommendations(jobId: string, userId?: string, orgId?: string): Promise<void> {
-    try {
-      const startTime = Date.now();
-
-      const [snapshot, allRates, monthlyForecast] = await Promise.all([
-        this.getFinancialSnapshot(),
-        this.getMarketRates(),
-        this.getMonthlyForecast(),
-      ]);
-
-      this.debug('background_snapshot_summary', {
-        job_id: jobId,
-        operating_cash: snapshot.summary.operating_cash,
-        reserve_cash: snapshot.summary.reserve_cash,
-        total_all: snapshot.summary.total_all,
-        investment_accounts: snapshot.investment_accounts.length,
-      });
-
-      const messages = this.buildPromptMessages(snapshot, allRates, monthlyForecast);
-      const aiResponse = await this.callAI(messages);
-      const elapsed = Date.now() - startTime;
-
-      this.debug('background_final_response', {
-        job_id: jobId,
-        recommendation_count: aiResponse.recommendations.length,
-        has_assessment: !!aiResponse.overall_assessment,
-        elapsed_ms: elapsed,
-      });
-
-      // Check if the AI returned a graceful error (empty recommendations with error message)
-      const isGracefulError = aiResponse.recommendations.length === 0 &&
-        (aiResponse.overall_assessment?.includes('Unable to generate') ||
-         aiResponse.overall_assessment?.includes('invalid response'));
-
-      if (isGracefulError) {
-        await this.updateRecommendationError(jobId, aiResponse.overall_assessment);
-      } else {
-        await this.updateRecommendationComplete(jobId, aiResponse, userId, elapsed);
-      }
-
-      // Log AI usage (fire-and-forget)
-      this.logAIUsage(userId, orgId, aiResponse, elapsed).catch(() => {});
-
-      this.logger.log(`Background AI recommendation completed (job ${jobId}) in ${elapsed}ms`);
-    } catch (err: any) {
-      this.logger.error(`Background AI recommendation error (job ${jobId}): ${err.message}`);
-      await this.updateRecommendationError(jobId, err.message);
-    }
-  }
-
   /**
    * Save AI recommendation result to tenant schema.
-   * @deprecated Use triggerAIRecommendations() for async flow instead
    */
   private async saveRecommendation(aiResponse: AIResponse, userId: string | undefined, elapsed: number): Promise<void> {
     try {
-      await this.ensureStatusColumn();
       await this.tenant.query(
         `INSERT INTO ai_recommendations
-         (recommendations_json, overall_assessment, risk_notes, requested_by, response_time_ms, status)
-         VALUES ($1, $2, $3, $4, $5, 'complete')`,
+         (recommendations_json, overall_assessment, risk_notes, requested_by, response_time_ms)
+         VALUES ($1, $2, $3, $4, $5)`,
         [
           JSON.stringify(aiResponse),
           aiResponse.overall_assessment || '',
@@ -1093,7 +873,7 @@ Based on this complete financial picture INCLUDING the 12-month cash flow foreca
             'Content-Type': 'application/json',
             'Content-Length': Buffer.byteLength(bodyString, 'utf-8'),
           },
-          timeout: 600000, // 10 minute timeout
+          timeout: 300000, // 5 minute timeout
         };
 
         const req = https.request(options, (res) => {
@@ -1107,7 +887,7 @@ Based on this complete financial picture INCLUDING the 12-month cash flow foreca
         req.on('error', (err) => reject(err));
         req.on('timeout', () => {
           req.destroy();
-          reject(new Error(`Request timed out after 600s`));
+          reject(new Error(`Request timed out after 300s`));
         });
 
         req.write(bodyString);

backend/src/modules/invoices/invoices.controller.ts

@@ -16,6 +16,11 @@ export class InvoicesController {
   @Get(':id')
   findOne(@Param('id') id: string) { return this.invoicesService.findOne(id); }
 
+  @Post('generate-preview')
+  generatePreview(@Body() dto: { month: number; year: number }) {
+    return this.invoicesService.generatePreview(dto);
+  }
+
   @Post('generate-bulk')
   generateBulk(@Body() dto: { month: number; year: number }, @Request() req: any) {
     return this.invoicesService.generateBulk(dto, req.user.sub);

backend/src/modules/invoices/invoices.service.ts

@@ -1,33 +1,135 @@
 import { Injectable, NotFoundException, BadRequestException } from '@nestjs/common';
 import { TenantService } from '../../database/tenant.service';
 
+const MONTH_NAMES = [
+  '', 'January', 'February', 'March', 'April', 'May', 'June',
+  'July', 'August', 'September', 'October', 'November', 'December',
+];
+
+const MONTH_ABBREV = [
+  '', 'Jan', 'Feb', 'Mar', 'Apr', 'May', 'Jun',
+  'Jul', 'Aug', 'Sep', 'Oct', 'Nov', 'Dec',
+];
+
 @Injectable()
 export class InvoicesService {
   constructor(private tenant: TenantService) {}
 
   async findAll() {
     return this.tenant.query(`
-      SELECT i.*, u.unit_number,
+      SELECT i.*, u.unit_number, u.owner_name, ag.name as assessment_group_name, ag.frequency,
         (i.amount - i.amount_paid) as balance_due
       FROM invoices i
       JOIN units u ON u.id = i.unit_id
+      LEFT JOIN assessment_groups ag ON ag.id = i.assessment_group_id
       ORDER BY i.invoice_date DESC, i.invoice_number DESC
     `);
   }
 
   async findOne(id: string) {
     const rows = await this.tenant.query(`
-      SELECT i.*, u.unit_number FROM invoices i
+      SELECT i.*, u.unit_number, u.owner_name FROM invoices i
       JOIN units u ON u.id = i.unit_id WHERE i.id = $1`, [id]);
     if (!rows.length) throw new NotFoundException('Invoice not found');
     return rows[0];
   }
 
-  async generateBulk(dto: { month: number; year: number }, userId: string) {
-    const units = await this.tenant.query(
-      `SELECT * FROM units WHERE status = 'active' AND monthly_assessment > 0`,
+  /**
+   * Calculate billing period based on frequency and the billing month.
+   */
+  private calculatePeriod(frequency: string, month: number, year: number): { start: string; end: string; description: string } {
+    switch (frequency) {
+      case 'quarterly': {
+        // Period covers 3 months starting from the billing month
+        const startDate = new Date(year, month - 1, 1);
+        const endDate = new Date(year, month + 2, 0); // last day of month+2
+        const endMonth = month + 2 > 12 ? month + 2 - 12 : month + 2;
+        const quarter = Math.ceil(month / 3);
+        return {
+          start: startDate.toISOString().split('T')[0],
+          end: endDate.toISOString().split('T')[0],
+          description: `Q${quarter} ${year} Assessment (${MONTH_ABBREV[month]}-${MONTH_ABBREV[endMonth]})`,
+        };
+      }
+      case 'annual': {
+        const startDate = new Date(year, 0, 1);
+        const endDate = new Date(year, 11, 31);
+        return {
+          start: startDate.toISOString().split('T')[0],
+          end: endDate.toISOString().split('T')[0],
+          description: `Annual Assessment ${year}`,
+        };
+      }
+      default: { // monthly
+        const startDate = new Date(year, month - 1, 1);
+        const endDate = new Date(year, month, 0); // last day of month
+        return {
+          start: startDate.toISOString().split('T')[0],
+          end: endDate.toISOString().split('T')[0],
+          description: `Monthly Assessment - ${MONTH_NAMES[month]} ${year}`,
+        };
+      }
+    }
+  }
+
+  /**
+   * Preview which groups/units will be billed for a given month/year.
+   */
+  async generatePreview(dto: { month: number; year: number }) {
+    const allGroups = await this.tenant.query(
+      `SELECT ag.*, (SELECT COUNT(*) FROM units u WHERE u.assessment_group_id = ag.id AND u.status = 'active') as active_units
+       FROM assessment_groups ag WHERE ag.is_active = true ORDER BY ag.name`,
     );
-    if (!units.length) throw new BadRequestException('No active units with assessments found');
+
+    const groups = allGroups.map((g: any) => {
+      const dueMonths: number[] = g.due_months || [1,2,3,4,5,6,7,8,9,10,11,12];
+      const isBillingMonth = dueMonths.includes(dto.month);
+      const activeUnits = parseInt(g.active_units || '0');
+      const totalAmount = isBillingMonth
+        ? (parseFloat(g.regular_assessment) + parseFloat(g.special_assessment || '0')) * activeUnits
+        : 0;
+      const period = this.calculatePeriod(g.frequency || 'monthly', dto.month, dto.year);
+
+      return {
+        id: g.id,
+        name: g.name,
+        frequency: g.frequency || 'monthly',
+        due_months: dueMonths,
+        active_units: activeUnits,
+        regular_assessment: g.regular_assessment,
+        special_assessment: g.special_assessment,
+        is_billing_month: isBillingMonth,
+        total_amount: totalAmount,
+        period_description: period.description,
+      };
+    });
+
+    const billableGroups = groups.filter((g: any) => g.is_billing_month && g.active_units > 0);
+    const totalInvoices = billableGroups.reduce((sum: number, g: any) => sum + g.active_units, 0);
+    const totalAmount = billableGroups.reduce((sum: number, g: any) => sum + g.total_amount, 0);
+
+    return {
+      month: dto.month,
+      year: dto.year,
+      month_name: MONTH_NAMES[dto.month],
+      groups,
+      summary: { total_groups_billing: billableGroups.length, total_invoices: totalInvoices, total_amount: totalAmount },
+    };
+  }
+
+  /**
+   * Generate invoices for all assessment groups where the given month is a billing month.
+   */
+  async generateBulk(dto: { month: number; year: number }, userId: string) {
+    // Get assessment groups where this month is a billing month
+    const groups = await this.tenant.query(
+      `SELECT * FROM assessment_groups WHERE is_active = true AND $1 = ANY(due_months)`,
+      [dto.month],
+    );
+
+    if (!groups.length) {
+      throw new BadRequestException(`No assessment groups have billing scheduled for ${MONTH_NAMES[dto.month]}`);
+    }
 
     // Get or create fiscal period
     let fp = await this.tenant.query(
@@ -41,9 +143,32 @@ export class InvoicesService {
     }
     const fiscalPeriodId = fp[0].id;
 
-    const invoiceDate = new Date(dto.year, dto.month - 1, 1);
-    const dueDate = new Date(dto.year, dto.month - 1, 15);
+    // Look up GL accounts once
+    const arAccount = await this.tenant.query(`SELECT id FROM accounts WHERE account_number = '1200'`);
+    const incomeAccount = await this.tenant.query(`SELECT id FROM accounts WHERE account_number = '4000'`);
+
     let created = 0;
+    const groupResults: any[] = [];
+
+    for (const group of groups) {
+      // Get active units in this assessment group
+      const units = await this.tenant.query(
+        `SELECT * FROM units WHERE status = 'active' AND assessment_group_id = $1`,
+        [group.id],
+      );
+
+      if (!units.length) continue;
+
+      const frequency = group.frequency || 'monthly';
+      const period = this.calculatePeriod(frequency, dto.month, dto.year);
+      const dueDay = Math.min(group.due_day || 1, 28);
+      const invoiceDate = new Date(dto.year, dto.month - 1, 1);
+      const dueDate = new Date(dto.year, dto.month - 1, dueDay);
+
+      // Use the group's assessment amount (full period amount, not monthly equivalent)
+      const assessmentAmount = parseFloat(group.regular_assessment) + parseFloat(group.special_assessment || '0');
+
+      let groupCreated = 0;
 
       for (const unit of units) {
         const invNum = `INV-${dto.year}${String(dto.month).padStart(2, '0')}-${unit.unit_number}`;
@@ -54,19 +179,24 @@ export class InvoicesService {
         );
         if (existing.length) continue;
 
-      // Create the invoice
+        // Use unit-level override if set, otherwise use group amount
+        const unitAmount = unit.monthly_assessment && parseFloat(unit.monthly_assessment) > 0
+          ? (frequency === 'monthly'
+              ? parseFloat(unit.monthly_assessment)
+              : frequency === 'quarterly'
+                ? parseFloat(unit.monthly_assessment) * 3
+                : parseFloat(unit.monthly_assessment) * 12)
+          : assessmentAmount;
+
+        // Create the invoice with status 'pending' (no email sending capability)
         const inv = await this.tenant.query(
-        `INSERT INTO invoices (invoice_number, unit_id, invoice_date, due_date, invoice_type, description, amount, status)
-         VALUES ($1, $2, $3, $4, 'regular_assessment', $5, $6, 'sent') RETURNING id`,
+          `INSERT INTO invoices (invoice_number, unit_id, invoice_date, due_date, invoice_type, description, amount, status, period_start, period_end, assessment_group_id)
+           VALUES ($1, $2, $3, $4, 'regular_assessment', $5, $6, 'pending', $7, $8, $9) RETURNING id`,
           [invNum, unit.id, invoiceDate.toISOString().split('T')[0], dueDate.toISOString().split('T')[0],
-         `Monthly assessment - ${new Date(dto.year, dto.month - 1).toLocaleString('default', { month: 'long', year: 'numeric' })}`,
-         unit.monthly_assessment],
+           period.description, unitAmount, period.start, period.end, group.id],
         );
 
         // Create journal entry: DR Accounts Receivable, CR Assessment Income
-      const arAccount = await this.tenant.query(`SELECT id FROM accounts WHERE account_number = '1200'`);
-      const incomeAccount = await this.tenant.query(`SELECT id FROM accounts WHERE account_number = '4000'`);
-
         if (arAccount.length && incomeAccount.length) {
           const je = await this.tenant.query(
             `INSERT INTO journal_entries (entry_date, description, entry_type, fiscal_period_id, source_type, source_id, is_posted, posted_at, created_by)
@@ -75,16 +205,25 @@ export class InvoicesService {
           );
           await this.tenant.query(
             `INSERT INTO journal_entry_lines (journal_entry_id, account_id, debit, credit) VALUES ($1, $2, $3, 0), ($1, $4, 0, $3)`,
-          [je[0].id, arAccount[0].id, unit.monthly_assessment, incomeAccount[0].id],
+            [je[0].id, arAccount[0].id, unitAmount, incomeAccount[0].id],
           );
           await this.tenant.query(
             `UPDATE invoices SET journal_entry_id = $1 WHERE id = $2`, [je[0].id, inv[0].id],
           );
         }
         created++;
+        groupCreated++;
       }
 
-    return { created, month: dto.month, year: dto.year };
+      groupResults.push({
+        group_name: group.name,
+        frequency,
+        period: period.description,
+        invoices_created: groupCreated,
+      });
+    }
+
+    return { created, month: dto.month, year: dto.year, groups: groupResults };
   }
 
   async applyLateFees(dto: { grace_period_days: number; late_fee_amount: number }, userId: string) {
@@ -95,7 +234,7 @@ export class InvoicesService {
     const overdue = await this.tenant.query(`
       SELECT i.*, u.unit_number FROM invoices i
       JOIN units u ON u.id = i.unit_id
-      WHERE i.status IN ('sent', 'partial') AND i.due_date < $1
+      WHERE i.status IN ('pending', 'partial') AND i.due_date < $1
         AND NOT EXISTS (
           SELECT 1 FROM invoices lf WHERE lf.unit_id = i.unit_id
           AND lf.invoice_type = 'late_fee' AND lf.description LIKE '%' || i.invoice_number || '%'
@@ -109,7 +248,7 @@ export class InvoicesService {
       const lfNum = `LF-${inv.invoice_number}`;
       await this.tenant.query(
         `INSERT INTO invoices (invoice_number, unit_id, invoice_date, due_date, invoice_type, description, amount, status)
-         VALUES ($1, $2, CURRENT_DATE, CURRENT_DATE + INTERVAL '15 days', 'late_fee', $3, $4, 'sent')`,
+         VALUES ($1, $2, CURRENT_DATE, CURRENT_DATE + INTERVAL '15 days', 'late_fee', $3, $4, 'pending')`,
         [lfNum, inv.unit_id, `Late fee for invoice ${inv.invoice_number}`, dto.late_fee_amount],
       );
       applied++;

backend/src/modules/payments/payments.controller.ts

@@ -1,4 +1,4 @@
-import { Controller, Get, Post, Body, Param, UseGuards, Request } from '@nestjs/common';
+import { Controller, Get, Post, Put, Delete, Body, Param, UseGuards, Request } from '@nestjs/common';
 import { ApiTags, ApiBearerAuth } from '@nestjs/swagger';
 import { JwtAuthGuard } from '../auth/guards/jwt-auth.guard';
 import { PaymentsService } from './payments.service';
@@ -18,4 +18,12 @@ export class PaymentsController {
 
   @Post()
   create(@Body() dto: any, @Request() req: any) { return this.paymentsService.create(dto, req.user.sub); }
+
+  @Put(':id')
+  update(@Param('id') id: string, @Body() dto: any, @Request() req: any) {
+    return this.paymentsService.update(id, dto, req.user.sub);
+  }
+
+  @Delete(':id')
+  delete(@Param('id') id: string) { return this.paymentsService.delete(id); }
 }

backend/src/modules/payments/payments.service.ts

@@ -74,17 +74,95 @@ export class PaymentsService {
       await this.tenant.query(`UPDATE payments SET journal_entry_id = $1 WHERE id = $2`, [je[0].id, payment[0].id]);
     }
 
-    // Update invoice if linked
+    // Update invoice if linked — use explicit cast to avoid PostgreSQL type inference error
     if (invoice) {
       const newPaid = parseFloat(invoice.amount_paid) + parseFloat(dto.amount);
       const invoiceAmt = parseFloat(invoice.amount);
       const newStatus = newPaid >= invoiceAmt ? 'paid' : 'partial';
       await this.tenant.query(
-        `UPDATE invoices SET amount_paid = $1, status = $2, paid_at = CASE WHEN $2 = 'paid' THEN NOW() ELSE paid_at END, updated_at = NOW() WHERE id = $3`,
-        [newPaid, newStatus, invoice.id],
+        `UPDATE invoices SET amount_paid = $1, status = $2::VARCHAR, paid_at = CASE WHEN $3::VARCHAR = 'paid' THEN NOW() ELSE paid_at END, updated_at = NOW() WHERE id = $4`,
+        [newPaid, newStatus, newStatus, invoice.id],
       );
     }
 
     return payment[0];
   }
+
+  async update(id: string, dto: any, userId: string) {
+    const existing = await this.findOne(id);
+
+    const sets: string[] = [];
+    const params: any[] = [];
+    let idx = 1;
+
+    if (dto.payment_date !== undefined) { sets.push(`payment_date = $${idx++}`); params.push(dto.payment_date); }
+    if (dto.amount !== undefined) { sets.push(`amount = $${idx++}`); params.push(dto.amount); }
+    if (dto.payment_method !== undefined) { sets.push(`payment_method = $${idx++}`); params.push(dto.payment_method); }
+    if (dto.reference_number !== undefined) { sets.push(`reference_number = $${idx++}`); params.push(dto.reference_number); }
+    if (dto.notes !== undefined) { sets.push(`notes = $${idx++}`); params.push(dto.notes); }
+
+    if (!sets.length) return this.findOne(id);
+
+    params.push(id);
+    await this.tenant.query(
+      `UPDATE payments SET ${sets.join(', ')} WHERE id = $${idx} RETURNING *`,
+      params,
+    );
+
+    // If amount changed and payment is linked to an invoice, recalculate invoice totals
+    if (dto.amount !== undefined && existing.invoice_id) {
+      await this.recalculateInvoice(existing.invoice_id);
+    }
+
+    return this.findOne(id);
+  }
+
+  async delete(id: string) {
+    const payment = await this.findOne(id);
+    const invoiceId = payment.invoice_id;
+
+    // Delete associated journal entry lines and journal entry
+    if (payment.journal_entry_id) {
+      await this.tenant.query('DELETE FROM journal_entry_lines WHERE journal_entry_id = $1', [payment.journal_entry_id]);
+      await this.tenant.query('DELETE FROM journal_entries WHERE id = $1', [payment.journal_entry_id]);
+    }
+
+    // Delete the payment
+    await this.tenant.query('DELETE FROM payments WHERE id = $1', [id]);
+
+    // Recalculate invoice totals if payment was linked
+    if (invoiceId) {
+      await this.recalculateInvoice(invoiceId);
+    }
+
+    return { success: true };
+  }
+
+  private async recalculateInvoice(invoiceId: string) {
+    // Sum all remaining payments for this invoice
+    const result = await this.tenant.query(
+      'SELECT COALESCE(SUM(amount), 0) as total_paid FROM payments WHERE invoice_id = $1',
+      [invoiceId],
+    );
+    const totalPaid = parseFloat(result[0].total_paid);
+
+    // Get the invoice amount
+    const inv = await this.tenant.query('SELECT amount FROM invoices WHERE id = $1', [invoiceId]);
+    if (!inv.length) return;
+
+    const invoiceAmt = parseFloat(inv[0].amount);
+    let newStatus: string;
+    if (totalPaid >= invoiceAmt) {
+      newStatus = 'paid';
+    } else if (totalPaid > 0) {
+      newStatus = 'partial';
+    } else {
+      newStatus = 'pending';
+    }
+
+    await this.tenant.query(
+      `UPDATE invoices SET amount_paid = $1, status = $2::VARCHAR, paid_at = CASE WHEN $3::VARCHAR = 'paid' THEN NOW() ELSE NULL END, updated_at = NOW() WHERE id = $4`,
+      [totalPaid, newStatus, newStatus, invoiceId],
+    );
+  }
 }

db/migrations/011-invoice-billing-frequency.sql

@@ -0,0 +1,57 @@
+-- Migration 011: Add billing frequency support to invoices
+-- Adds due_months and due_day to assessment_groups
+-- Adds period_start, period_end, assessment_group_id to invoices
+
+DO $$
+DECLARE
+  v_schema TEXT;
+BEGIN
+  FOR v_schema IN
+    SELECT schema_name FROM information_schema.schemata
+    WHERE schema_name LIKE 'tenant_%'
+  LOOP
+    -- Add due_months and due_day to assessment_groups
+    EXECUTE format('
+      ALTER TABLE %I.assessment_groups
+        ADD COLUMN IF NOT EXISTS due_months INTEGER[] DEFAULT ''{1,2,3,4,5,6,7,8,9,10,11,12}'',
+        ADD COLUMN IF NOT EXISTS due_day INTEGER DEFAULT 1
+    ', v_schema);
+
+    -- Add period tracking and assessment group link to invoices
+    EXECUTE format('
+      ALTER TABLE %I.invoices
+        ADD COLUMN IF NOT EXISTS period_start DATE,
+        ADD COLUMN IF NOT EXISTS period_end DATE,
+        ADD COLUMN IF NOT EXISTS assessment_group_id UUID
+    ', v_schema);
+
+    -- Backfill due_months based on existing frequency values
+    EXECUTE format('
+      UPDATE %I.assessment_groups
+      SET due_months = CASE frequency
+        WHEN ''quarterly'' THEN ''{1,4,7,10}''::INTEGER[]
+        WHEN ''annual'' THEN ''{1}''::INTEGER[]
+        ELSE ''{1,2,3,4,5,6,7,8,9,10,11,12}''::INTEGER[]
+      END
+      WHERE due_months IS NULL OR due_months = ''{1,2,3,4,5,6,7,8,9,10,11,12}''
+        AND frequency != ''monthly''
+    ', v_schema);
+
+    -- Backfill period_start/period_end for existing invoices (all monthly)
+    EXECUTE format('
+      UPDATE %I.invoices
+      SET period_start = invoice_date,
+          period_end = (invoice_date + INTERVAL ''1 month'' - INTERVAL ''1 day'')::DATE
+      WHERE period_start IS NULL AND invoice_type = ''regular_assessment''
+    ', v_schema);
+
+    -- Backfill assessment_group_id on existing invoices from units
+    EXECUTE format('
+      UPDATE %I.invoices i
+      SET assessment_group_id = u.assessment_group_id
+      FROM %I.units u
+      WHERE i.unit_id = u.id AND i.assessment_group_id IS NULL
+    ', v_schema, v_schema);
+
+  END LOOP;
+END $$;

db/migrations/012-invoice-status-pending.sql

@@ -0,0 +1,33 @@
+-- Migration 012: Replace 'sent' status with 'pending' for invoices
+-- 'sent' implied email delivery which doesn't exist; 'pending' is more accurate
+
+DO $$
+DECLARE
+  v_schema TEXT;
+  v_constraint TEXT;
+BEGIN
+  FOR v_schema IN
+    SELECT schema_name FROM information_schema.schemata
+    WHERE schema_name LIKE 'tenant_%'
+  LOOP
+    -- Find and drop the existing status check constraint
+    SELECT constraint_name INTO v_constraint
+    FROM information_schema.table_constraints
+    WHERE table_schema = v_schema
+      AND table_name = 'invoices'
+      AND constraint_type = 'CHECK'
+      AND constraint_name LIKE '%status%';
+
+    IF v_constraint IS NOT NULL THEN
+      EXECUTE format('ALTER TABLE %I.invoices DROP CONSTRAINT %I', v_schema, v_constraint);
+    END IF;
+
+    -- Add new constraint that includes 'pending'
+    EXECUTE format('ALTER TABLE %I.invoices ADD CONSTRAINT invoices_status_check CHECK (status IN (
+      ''draft'', ''pending'', ''sent'', ''paid'', ''partial'', ''overdue'', ''void'', ''written_off''
+    ))', v_schema);
+
+    -- Convert existing 'sent' invoices to 'pending'
+    EXECUTE format('UPDATE %I.invoices SET status = ''pending'' WHERE status = ''sent''', v_schema);
+  END LOOP;
+END $$;

db/seed/seed.sql

@@ -204,7 +204,10 @@ CREATE TABLE IF NOT EXISTS %I.assessment_groups (
   special_assessment DECIMAL(10,2) DEFAULT 0.00,
   unit_count INTEGER DEFAULT 0,
   frequency VARCHAR(20) DEFAULT ''monthly'',
+  due_months INTEGER[] DEFAULT ''{1,2,3,4,5,6,7,8,9,10,11,12}'',
+  due_day INTEGER DEFAULT 1,
   is_active BOOLEAN DEFAULT TRUE,
+  is_default BOOLEAN DEFAULT FALSE,
   created_at TIMESTAMPTZ DEFAULT NOW(),
   updated_at TIMESTAMPTZ DEFAULT NOW()
 )', v_schema);
@@ -244,6 +247,9 @@ CREATE TABLE IF NOT EXISTS %I.invoices (
   amount DECIMAL(10,2) NOT NULL,
   amount_paid DECIMAL(10,2) DEFAULT 0.00,
   status VARCHAR(20) DEFAULT ''draft'',
+  period_start DATE,
+  period_end DATE,
+  assessment_group_id UUID,
   journal_entry_id UUID,
   sent_at TIMESTAMPTZ,
   paid_at TIMESTAMPTZ,
@@ -443,10 +449,10 @@ END LOOP;
 -- ============================================================
 -- 4b. Seed Assessment Groups
 -- ============================================================
-EXECUTE format('INSERT INTO %I.assessment_groups (name, description, regular_assessment, special_assessment, unit_count) VALUES
-  (''Single Family Homes'', ''Standard single family detached homes (Units 1-20)'', 350.00, 0.00, 20),
-  (''Patio Homes'', ''Medium-sized patio homes (Units 21-35)'', 425.00, 0.00, 15),
-  (''Estate Lots'', ''Large estate lots (Units 36-50)'', 500.00, 75.00, 15)
+EXECUTE format('INSERT INTO %I.assessment_groups (name, description, regular_assessment, special_assessment, unit_count, frequency, due_months, due_day) VALUES
+  (''Single Family Homes'', ''Standard single family detached homes (Units 1-20)'', 350.00, 0.00, 20, ''monthly'', ''{1,2,3,4,5,6,7,8,9,10,11,12}'', 15),
+  (''Patio Homes'', ''Medium-sized patio homes (Units 21-35)'', 1275.00, 0.00, 15, ''quarterly'', ''{1,4,7,10}'', 1),
+  (''Estate Lots'', ''Large estate lots (Units 36-50)'', 6000.00, 900.00, 15, ''annual'', ''{3}'', 1)
 ', v_schema);
 
 -- ============================================================

frontend/src/pages/assessment-groups/AssessmentGroupsPage.tsx

@@ -2,6 +2,7 @@ import { useState } from 'react';
 import {
   Title, Text, Card, Table, SimpleGrid, Group, Stack, Badge, Loader, Center,
   ThemeIcon, Button, Modal, TextInput, NumberInput, Textarea, Select, ActionIcon, Tooltip,
+  MultiSelect,
 } from '@mantine/core';
 import { useForm } from '@mantine/form';
 import { useDisclosure } from '@mantine/hooks';
@@ -21,6 +22,8 @@ interface AssessmentGroup {
   special_assessment: string;
   unit_count: number;
   frequency: string;
+  due_months: number[];
+  due_day: number;
   actual_unit_count: string;
   monthly_operating_income: string;
   monthly_reserve_income: string;
@@ -49,6 +52,29 @@ const frequencyColors: Record<string, string> = {
   annual: 'violet',
 };
 
+const MONTH_OPTIONS = [
+  { value: '1', label: 'January' },
+  { value: '2', label: 'February' },
+  { value: '3', label: 'March' },
+  { value: '4', label: 'April' },
+  { value: '5', label: 'May' },
+  { value: '6', label: 'June' },
+  { value: '7', label: 'July' },
+  { value: '8', label: 'August' },
+  { value: '9', label: 'September' },
+  { value: '10', label: 'October' },
+  { value: '11', label: 'November' },
+  { value: '12', label: 'December' },
+];
+
+const MONTH_ABBREV = ['', 'Jan', 'Feb', 'Mar', 'Apr', 'May', 'Jun', 'Jul', 'Aug', 'Sep', 'Oct', 'Nov', 'Dec'];
+
+const DEFAULT_DUE_MONTHS: Record<string, string[]> = {
+  monthly: ['1','2','3','4','5','6','7','8','9','10','11','12'],
+  quarterly: ['1','4','7','10'],
+  annual: ['1'],
+};
+
 export function AssessmentGroupsPage() {
   const [opened, { open, close }] = useDisclosure(false);
   const [editing, setEditing] = useState<AssessmentGroup | null>(null);
@@ -73,18 +99,31 @@ export function AssessmentGroupsPage() {
       specialAssessment: 0,
       unitCount: 0,
       frequency: 'monthly',
+      dueMonths: DEFAULT_DUE_MONTHS.monthly,
+      dueDay: 1,
     },
     validate: {
       name: (v) => (v.length > 0 ? null : 'Required'),
       regularAssessment: (v) => (v >= 0 ? null : 'Must be >= 0'),
+      dueMonths: (v, values) => {
+        if (values.frequency === 'quarterly' && v.length !== 4) return 'Quarterly requires exactly 4 months';
+        if (values.frequency === 'annual' && v.length !== 1) return 'Annual requires exactly 1 month';
+        return null;
+      },
+      dueDay: (v) => (v >= 1 && v <= 28 ? null : 'Must be 1-28'),
     },
   });
 
   const saveMutation = useMutation({
-    mutationFn: (values: any) =>
-      editing
-        ? api.put(`/assessment-groups/${editing.id}`, values)
-        : api.post('/assessment-groups', values),
+    mutationFn: (values: any) => {
+      const payload = {
+        ...values,
+        dueMonths: values.dueMonths.map(Number),
+      };
+      return editing
+        ? api.put(`/assessment-groups/${editing.id}`, payload)
+        : api.post('/assessment-groups', payload);
+    },
     onSuccess: () => {
       queryClient.invalidateQueries({ queryKey: ['assessment-groups'] });
       queryClient.invalidateQueries({ queryKey: ['assessment-groups-summary'] });
@@ -121,6 +160,9 @@ export function AssessmentGroupsPage() {
 
   const handleEdit = (group: AssessmentGroup) => {
     setEditing(group);
+    const dueMonths = group.due_months
+      ? group.due_months.map(String)
+      : DEFAULT_DUE_MONTHS[group.frequency] || DEFAULT_DUE_MONTHS.monthly;
     form.setValues({
       name: group.name,
       description: group.description || '',
@@ -128,6 +170,8 @@ export function AssessmentGroupsPage() {
       specialAssessment: parseFloat(group.special_assessment || '0'),
       unitCount: group.unit_count || 0,
       frequency: group.frequency || 'monthly',
+      dueMonths,
+      dueDay: group.due_day || 1,
     });
     open();
   };
@@ -138,6 +182,12 @@ export function AssessmentGroupsPage() {
     open();
   };
 
+  const handleFrequencyChange = (value: string | null) => {
+    if (!value) return;
+    form.setFieldValue('frequency', value);
+    form.setFieldValue('dueMonths', DEFAULT_DUE_MONTHS[value] || DEFAULT_DUE_MONTHS.monthly);
+  };
+
   const fmt = (v: string | number) =>
     parseFloat(String(v || '0')).toLocaleString('en-US', { style: 'currency', currency: 'USD' });
 
@@ -149,6 +199,11 @@ export function AssessmentGroupsPage() {
     }
   };
 
+  const formatDueMonths = (months: number[], frequency: string) => {
+    if (!months || frequency === 'monthly') return 'Every month';
+    return months.map((m) => MONTH_ABBREV[m]).join(', ');
+  };
+
   if (isLoading) return <Center h={300}><Loader /></Center>;
 
   return (
@@ -219,6 +274,7 @@ export function AssessmentGroupsPage() {
               <Table.Th>Group Name</Table.Th>
               <Table.Th ta="center">Units</Table.Th>
               <Table.Th>Frequency</Table.Th>
+              <Table.Th>Due Months</Table.Th>
               <Table.Th ta="right">Regular Assessment</Table.Th>
               <Table.Th ta="right">Special Assessment</Table.Th>
               <Table.Th ta="right">Monthly Equiv.</Table.Th>
@@ -229,7 +285,7 @@ export function AssessmentGroupsPage() {
           <Table.Tbody>
             {groups.length === 0 && (
               <Table.Tr>
-                <Table.Td colSpan={8}>
+                <Table.Td colSpan={9}>
                   <Text ta="center" c="dimmed" py="lg">
                     No assessment groups yet. Create groups like "Single Family Homes", "Condos", etc.
                   </Text>
@@ -263,6 +319,9 @@ export function AssessmentGroupsPage() {
                     {frequencyLabels[g.frequency] || 'Monthly'}
                   </Badge>
                 </Table.Td>
+                <Table.Td>
+                  <Text size="xs" c="dimmed">{formatDueMonths(g.due_months, g.frequency)}</Text>
+                </Table.Td>
                 <Table.Td ta="right" ff="monospace">
                   {fmt(g.regular_assessment)}{freqSuffix(g.frequency)}
                 </Table.Td>
@@ -322,8 +381,22 @@ export function AssessmentGroupsPage() {
                 { value: 'quarterly', label: 'Quarterly' },
                 { value: 'annual', label: 'Annual' },
               ]}
-              {...form.getInputProps('frequency')}
+              value={form.values.frequency}
+              onChange={handleFrequencyChange}
             />
+            {form.values.frequency !== 'monthly' && (
+              <MultiSelect
+                label={form.values.frequency === 'quarterly' ? 'Billing Quarters (select 4 months)' : 'Due Month'}
+                description={form.values.frequency === 'quarterly'
+                  ? 'Select the first month of each quarter when assessments are due'
+                  : 'Select the month when the annual assessment is due'}
+                data={MONTH_OPTIONS}
+                value={form.values.dueMonths}
+                onChange={(v) => form.setFieldValue('dueMonths', v)}
+                error={form.errors.dueMonths}
+                maxValues={form.values.frequency === 'annual' ? 1 : 4}
+              />
+            )}
             <Group grow>
               <NumberInput
                 label={`Regular Assessment (per unit${freqSuffix(form.values.frequency)})`}
@@ -340,7 +413,16 @@ export function AssessmentGroupsPage() {
                 {...form.getInputProps('specialAssessment')}
               />
             </Group>
+            <Group grow>
               <NumberInput label="Expected Unit Count" min={0} {...form.getInputProps('unitCount')} />
+              <NumberInput
+                label="Due Day of Month"
+                description="Day invoices are due (1-28)"
+                min={1}
+                max={28}
+                {...form.getInputProps('dueDay')}
+              />
+            </Group>
             <Button type="submit" loading={saveMutation.isPending}>
               {editing ? 'Update' : 'Create'}
             </Button>

frontend/src/pages/dashboard/DashboardPage.tsx

@@ -16,8 +16,8 @@ import {
   IconRefresh,
   IconInfoCircle,
 } from '@tabler/icons-react';
-import { useState, useCallback } from 'react';
-import { useQuery, useQueryClient } from '@tanstack/react-query';
+import { useState } from 'react';
+import { useQuery, useMutation, useQueryClient } from '@tanstack/react-query';
 import { useAuthStore } from '../../stores/authStore';
 import api from '../../services/api';
 
@@ -313,9 +313,9 @@ export function DashboardPage() {
   const currentOrg = useAuthStore((s) => s.currentOrg);
   const queryClient = useQueryClient();
 
-  // Track whether a refresh is in progress (per score type) for async polling
-  const [operatingRefreshing, setOperatingRefreshing] = useState(false);
-  const [reserveRefreshing, setReserveRefreshing] = useState(false);
+  // Track whether last refresh attempt failed (per score type)
+  const [operatingFailed, setOperatingFailed] = useState(false);
+  const [reserveFailed, setReserveFailed] = useState(false);
 
   const { data, isLoading } = useQuery<DashboardData>({
     queryKey: ['dashboard'],
@@ -327,66 +327,33 @@ export function DashboardPage() {
     queryKey: ['health-scores'],
     queryFn: async () => { const { data } = await api.get('/health-scores/latest'); return data; },
     enabled: !!currentOrg,
-    // Poll every 3 seconds while a refresh is in progress
-    refetchInterval: (operatingRefreshing || reserveRefreshing) ? 3000 : false,
   });
 
-  // Async refresh handlers — trigger the backend and poll for results
-  const handleRefreshOperating = useCallback(async () => {
-    const prevId = healthScores?.operating?.id;
-    setOperatingRefreshing(true);
-    try {
-      await api.post('/health-scores/calculate/operating');
-    } catch {
-      // Trigger failed at network level — polling will pick up any backend-saved error
-    }
-    // Start polling — watch for the health score to change (new id or updated timestamp)
-    const pollUntilDone = () => {
-      const checkInterval = setInterval(async () => {
-        try {
-          const { data: latest } = await api.get('/health-scores/latest');
-          const newScore = latest?.operating;
-          if (newScore && newScore.id !== prevId) {
-            setOperatingRefreshing(false);
-            queryClient.setQueryData(['health-scores'], latest);
-            clearInterval(checkInterval);
-          }
-        } catch {
-          // Keep polling
-        }
-      }, 3000);
-      // Safety timeout — stop polling after 11 minutes
-      setTimeout(() => { clearInterval(checkInterval); setOperatingRefreshing(false); }, 660000);
-    };
-    pollUntilDone();
-  }, [healthScores?.operating?.id, queryClient]);
+  // Separate mutations for each score type
+  const recalcOperatingMutation = useMutation({
+    mutationFn: () => api.post('/health-scores/calculate/operating'),
+    onSuccess: () => {
+      setOperatingFailed(false);
+      queryClient.invalidateQueries({ queryKey: ['health-scores'] });
+    },
+    onError: () => {
+      setOperatingFailed(true);
+      // Still refresh to get whatever the backend saved (could be cached data)
+      queryClient.invalidateQueries({ queryKey: ['health-scores'] });
+    },
+  });
 
-  const handleRefreshReserve = useCallback(async () => {
-    const prevId = healthScores?.reserve?.id;
-    setReserveRefreshing(true);
-    try {
-      await api.post('/health-scores/calculate/reserve');
-    } catch {
-      // Trigger failed at network level
-    }
-    const pollUntilDone = () => {
-      const checkInterval = setInterval(async () => {
-        try {
-          const { data: latest } = await api.get('/health-scores/latest');
-          const newScore = latest?.reserve;
-          if (newScore && newScore.id !== prevId) {
-            setReserveRefreshing(false);
-            queryClient.setQueryData(['health-scores'], latest);
-            clearInterval(checkInterval);
-          }
-        } catch {
-          // Keep polling
-        }
-      }, 3000);
-      setTimeout(() => { clearInterval(checkInterval); setReserveRefreshing(false); }, 660000);
-    };
-    pollUntilDone();
-  }, [healthScores?.reserve?.id, queryClient]);
+  const recalcReserveMutation = useMutation({
+    mutationFn: () => api.post('/health-scores/calculate/reserve'),
+    onSuccess: () => {
+      setReserveFailed(false);
+      queryClient.invalidateQueries({ queryKey: ['health-scores'] });
+    },
+    onError: () => {
+      setReserveFailed(true);
+      queryClient.invalidateQueries({ queryKey: ['health-scores'] });
+    },
+  });
 
   const fmt = (v: string | number) =>
     parseFloat(String(v || '0')).toLocaleString('en-US', { style: 'currency', currency: 'USD' });
@@ -424,9 +391,9 @@ export function DashboardPage() {
                   <IconHeartbeat size={20} />
                 </ThemeIcon>
               }
-              isRefreshing={operatingRefreshing}
-              onRefresh={handleRefreshOperating}
-              lastFailed={!!healthScores?.operating_last_failed}
+              isRefreshing={recalcOperatingMutation.isPending}
+              onRefresh={() => recalcOperatingMutation.mutate()}
+              lastFailed={operatingFailed || !!healthScores?.operating_last_failed}
             />
             <HealthScoreCard
               score={healthScores?.reserve || null}
@@ -436,9 +403,9 @@ export function DashboardPage() {
                   <IconHeartbeat size={20} />
                 </ThemeIcon>
               }
-              isRefreshing={reserveRefreshing}
-              onRefresh={handleRefreshReserve}
-              lastFailed={!!healthScores?.reserve_last_failed}
+              isRefreshing={recalcReserveMutation.isPending}
+              onRefresh={() => recalcReserveMutation.mutate()}
+              lastFailed={reserveFailed || !!healthScores?.reserve_last_failed}
             />
           </SimpleGrid>
 

frontend/src/pages/investment-planning/InvestmentPlanningPage.tsx

@@ -1,4 +1,4 @@
-import { useState, useEffect, useCallback } from 'react';
+import { useState, useEffect } from 'react';
 import {
   Title,
   Text,
@@ -33,7 +33,7 @@ import {
   IconChevronDown,
   IconChevronUp,
 } from '@tabler/icons-react';
-import { useQuery } from '@tanstack/react-query';
+import { useQuery, useMutation } from '@tanstack/react-query';
 import { notifications } from '@mantine/notifications';
 import api from '../../services/api';
 
@@ -107,9 +107,6 @@ interface SavedRecommendation {
   risk_notes: string[];
   response_time_ms: number;
   created_at: string;
-  status: 'processing' | 'complete' | 'error';
-  last_failed: boolean;
-  error_message?: string;
 }
 
 // ── Helpers ──
@@ -184,29 +181,14 @@ function RateTable({ rates, showTerm }: { rates: MarketRate[]; showTerm: boolean
 
 // ── Recommendations Display Component ──
 
-function RecommendationsDisplay({
-  aiResult,
-  lastUpdated,
-  lastFailed,
-}: {
-  aiResult: AIResponse;
-  lastUpdated?: string;
-  lastFailed?: boolean;
-}) {
+function RecommendationsDisplay({ aiResult, lastUpdated }: { aiResult: AIResponse; lastUpdated?: string }) {
   return (
     <Stack>
-      {/* Last Updated timestamp + failure message */}
+      {/* Last Updated timestamp */}
       {lastUpdated && (
-        <Stack gap={0} align="flex-end">
         <Text size="xs" c="dimmed" ta="right">
           Last updated: {new Date(lastUpdated).toLocaleString()}
         </Text>
-          {lastFailed && (
-            <Text size="10px" c="orange" fw={500} style={{ opacity: 0.85 }}>
-              last analysis failed — showing cached data
-            </Text>
-          )}
-        </Stack>
       )}
 
       {/* Overall Assessment */}
@@ -345,8 +327,9 @@ function RecommendationsDisplay({
 // ── Main Component ──
 
 export function InvestmentPlanningPage() {
+  const [aiResult, setAiResult] = useState<AIResponse | null>(null);
+  const [lastUpdated, setLastUpdated] = useState<string | null>(null);
   const [ratesExpanded, setRatesExpanded] = useState(true);
-  const [isTriggering, setIsTriggering] = useState(false);
 
   // Load financial snapshot on mount
   const { data: snapshot, isLoading: snapshotLoading } = useQuery<FinancialSnapshot>({
@@ -366,86 +349,50 @@ export function InvestmentPlanningPage() {
     },
   });
 
-  // Load saved recommendation — polls every 3s when processing
+  // Load saved recommendation on mount
   const { data: savedRec } = useQuery<SavedRecommendation | null>({
     queryKey: ['investment-planning-saved-recommendation'],
     queryFn: async () => {
       const { data } = await api.get('/investment-planning/saved-recommendation');
       return data;
     },
-    refetchInterval: (query) => {
-      const rec = query.state.data;
-      // Poll every 3 seconds while processing
-      if (rec?.status === 'processing') return 3000;
-      // Also poll if we just triggered (status may not be 'processing' yet)
-      if (isTriggering) return 3000;
-      return false;
-    },
   });
 
-  // Derive display state from saved recommendation
-  const isProcessing = savedRec?.status === 'processing' || isTriggering;
-  const lastFailed = savedRec?.last_failed || false;
-  const hasResults = savedRec && savedRec.status === 'complete' && savedRec.recommendations.length > 0;
-  const hasError = savedRec?.status === 'error' && !savedRec?.recommendations?.length;
-
-  // Clear triggering flag once backend confirms processing or completes
+  // Populate AI results from saved recommendation on load
   useEffect(() => {
-    if (isTriggering && savedRec?.status === 'processing') {
-      setIsTriggering(false);
+    if (savedRec && !aiResult) {
+      setAiResult({
+        recommendations: savedRec.recommendations,
+        overall_assessment: savedRec.overall_assessment,
+        risk_notes: savedRec.risk_notes,
+      });
+      setLastUpdated(savedRec.created_at);
     }
-    if (isTriggering && savedRec?.status === 'complete') {
-      setIsTriggering(false);
-    }
-  }, [savedRec?.status, isTriggering]);
+  }, [savedRec]); // eslint-disable-line react-hooks/exhaustive-deps
 
-  // Show notification when processing completes (transition from processing)
-  const prevStatusRef = useState<string | null>(null);
-  useEffect(() => {
-    const [prevStatus, setPrevStatus] = prevStatusRef;
-    if (prevStatus === 'processing' && savedRec?.status === 'complete') {
+  // AI recommendation (on-demand)
+  const aiMutation = useMutation({
+    mutationFn: async () => {
+      const { data } = await api.post('/investment-planning/recommendations', {}, { timeout: 300000 });
+      return data as AIResponse;
+    },
+    onSuccess: (data) => {
+      setAiResult(data);
+      setLastUpdated(new Date().toISOString());
+      if (data.recommendations.length > 0) {
         notifications.show({
-        message: `Generated ${savedRec.recommendations.length} investment recommendations`,
+          message: `Generated ${data.recommendations.length} investment recommendations`,
           color: 'green',
         });
       }
-    if (prevStatus === 'processing' && savedRec?.status === 'error') {
+    },
+    onError: (err: any) => {
       notifications.show({
-        message: savedRec.error_message || 'AI recommendation analysis failed',
+        message: err.response?.data?.message || 'Failed to get AI recommendations',
         color: 'red',
       });
-    }
-    setPrevStatus(savedRec?.status || null);
-  }, [savedRec?.status]); // eslint-disable-line react-hooks/exhaustive-deps
-
-  // Trigger AI recommendations (async — returns immediately)
-  const handleTriggerAI = useCallback(async () => {
-    setIsTriggering(true);
-    try {
-      await api.post('/investment-planning/recommendations');
-    } catch (err: any) {
-      setIsTriggering(false);
-      notifications.show({
-        message: err.response?.data?.message || 'Failed to start AI analysis',
-        color: 'red',
+    },
   });
-    }
-  }, []);
-
-  // Build AI result from saved recommendation for display
-  const aiResult: AIResponse | null = hasResults
-    ? {
-        recommendations: savedRec!.recommendations,
-        overall_assessment: savedRec!.overall_assessment,
-        risk_notes: savedRec!.risk_notes,
-      }
-    : (lastFailed && savedRec?.recommendations?.length)
-      ? {
-          recommendations: savedRec!.recommendations,
-          overall_assessment: savedRec!.overall_assessment,
-          risk_notes: savedRec!.risk_notes,
-        }
-      : null;
 
   if (snapshotLoading) {
     return (
@@ -698,8 +645,8 @@ export function InvestmentPlanningPage() {
           </Group>
           <Button
             leftSection={<IconSparkles size={16} />}
-            onClick={handleTriggerAI}
-            loading={isProcessing}
+            onClick={() => aiMutation.mutate()}
+            loading={aiMutation.isPending}
             variant="gradient"
             gradient={{ from: 'grape', to: 'violet' }}
           >
@@ -707,8 +654,8 @@ export function InvestmentPlanningPage() {
           </Button>
         </Group>
 
-        {/* Processing State */}
-        {isProcessing && (
+        {/* Loading State */}
+        {aiMutation.isPending && (
           <Center py="xl">
             <Stack align="center" gap="sm">
               <Loader size="lg" type="dots" />
@@ -716,32 +663,19 @@ export function InvestmentPlanningPage() {
                 Analyzing your financial data and market rates...
               </Text>
               <Text c="dimmed" size="xs">
-                You can navigate away — results will appear when ready
+                This may take a few minutes for complex tenant data
               </Text>
             </Stack>
           </Center>
         )}
 
-        {/* Error State (no cached data) */}
-        {hasError && !isProcessing && (
-          <Alert color="red" variant="light" title="Analysis Failed" mb="md">
-            <Text size="sm">
-              {savedRec?.error_message || 'The last AI analysis failed. Please try again.'}
-            </Text>
-          </Alert>
-        )}
-
-        {/* Results (with optional failure watermark) */}
-        {aiResult && !isProcessing && (
-          <RecommendationsDisplay
-            aiResult={aiResult}
-            lastUpdated={savedRec?.created_at || undefined}
-            lastFailed={lastFailed}
-          />
+        {/* Results */}
+        {aiResult && !aiMutation.isPending && (
+          <RecommendationsDisplay aiResult={aiResult} lastUpdated={lastUpdated || undefined} />
         )}
 
         {/* Empty State */}
-        {!aiResult && !isProcessing && !hasError && (
+        {!aiResult && !aiMutation.isPending && (
           <Paper p="xl" radius="sm" style={{ textAlign: 'center' }}>
             <ThemeIcon variant="light" color="grape" size={48} mx="auto" mb="md">
               <IconSparkles size={28} />

frontend/src/pages/invoices/InvoicesPage.tsx

@@ -1,13 +1,12 @@
-import { useState } from 'react';
+import { useState, useEffect } from 'react';
 import {
   Title, Table, Group, Button, Stack, Text, Badge, Modal,
-  NumberInput, Select, Loader, Center, Card,
+  NumberInput, Select, Loader, Center, Card, Alert,
 } from '@mantine/core';
-import { DateInput } from '@mantine/dates';
 import { useForm } from '@mantine/form';
 import { useDisclosure } from '@mantine/hooks';
 import { notifications } from '@mantine/notifications';
-import { IconFileInvoice, IconSend } from '@tabler/icons-react';
+import { IconSend, IconInfoCircle, IconCheck, IconX } from '@tabler/icons-react';
 import { useQuery, useMutation, useQueryClient } from '@tanstack/react-query';
 import api from '../../services/api';
 
@@ -15,15 +14,55 @@ interface Invoice {
   id: string; invoice_number: string; unit_number: string; unit_id: string;
   invoice_date: string; due_date: string; invoice_type: string;
   description: string; amount: string; amount_paid: string; balance_due: string;
-  status: string;
+  status: string; period_start: string; period_end: string;
+  assessment_group_name: string; frequency: string; owner_name: string;
+}
+
+interface PreviewGroup {
+  id: string;
+  name: string;
+  frequency: string;
+  active_units: number;
+  regular_assessment: string;
+  special_assessment: string;
+  is_billing_month: boolean;
+  total_amount: number;
+  period_description: string;
+}
+
+interface Preview {
+  month: number;
+  year: number;
+  month_name: string;
+  groups: PreviewGroup[];
+  summary: {
+    total_groups_billing: number;
+    total_invoices: number;
+    total_amount: number;
+  };
 }
 
 const statusColors: Record<string, string> = {
-  draft: 'gray', sent: 'blue', paid: 'green', partial: 'yellow', overdue: 'red', void: 'dark',
+  draft: 'gray', pending: 'blue', paid: 'green', partial: 'yellow', overdue: 'red', void: 'dark',
+};
+
+const frequencyColors: Record<string, string> = {
+  monthly: 'blue', quarterly: 'teal', annual: 'violet',
+};
+
+const fmt = (v: string | number) => parseFloat(String(v || '0')).toLocaleString('en-US', { style: 'currency', currency: 'USD' });
+
+/** Extract last name from "First Last" format */
+const getLastName = (ownerName: string | null) => {
+  if (!ownerName) return '-';
+  const parts = ownerName.trim().split(/\s+/);
+  return parts.length > 1 ? parts[parts.length - 1] : ownerName;
 };
 
 export function InvoicesPage() {
   const [bulkOpened, { open: openBulk, close: closeBulk }] = useDisclosure(false);
+  const [preview, setPreview] = useState<Preview | null>(null);
+  const [previewLoading, setPreviewLoading] = useState(false);
   const queryClient = useQueryClient();
 
   const { data: invoices = [], isLoading } = useQuery<Invoice[]>({
@@ -35,13 +74,36 @@ export function InvoicesPage() {
     initialValues: { month: new Date().getMonth() + 1, year: new Date().getFullYear() },
   });
 
+  // Fetch preview when month/year changes
+  const fetchPreview = async (month: number, year: number) => {
+    setPreviewLoading(true);
+    try {
+      const { data } = await api.post('/invoices/generate-preview', { month, year });
+      setPreview(data);
+    } catch {
+      setPreview(null);
+    }
+    setPreviewLoading(false);
+  };
+
+  useEffect(() => {
+    if (bulkOpened) {
+      fetchPreview(bulkForm.values.month, bulkForm.values.year);
+    }
+  }, [bulkOpened, bulkForm.values.month, bulkForm.values.year]);
+
   const bulkMutation = useMutation({
     mutationFn: (values: any) => api.post('/invoices/generate-bulk', values),
     onSuccess: (res) => {
       queryClient.invalidateQueries({ queryKey: ['invoices'] });
       queryClient.invalidateQueries({ queryKey: ['journal-entries'] });
-      notifications.show({ message: `Generated ${res.data.created} invoices`, color: 'green' });
+      const groupInfo = res.data.groups?.map((g: any) => `${g.group_name}: ${g.invoices_created}`).join(', ') || '';
+      notifications.show({
+        message: `Generated ${res.data.created} invoices${groupInfo ? ` (${groupInfo})` : ''}`,
+        color: 'green',
+      });
       closeBulk();
+      setPreview(null);
     },
     onError: (err: any) => { notifications.show({ message: err.response?.data?.message || 'Error', color: 'red' }); },
   });
@@ -54,8 +116,6 @@ export function InvoicesPage() {
     },
   });
 
-  const fmt = (v: string) => parseFloat(v || '0').toLocaleString('en-US', { style: 'currency', currency: 'USD' });
-
   if (isLoading) return <Center h={300}><Loader /></Center>;
 
   const totalOutstanding = invoices.filter(i => i.status !== 'paid' && i.status !== 'void').reduce((s, i) => s + parseFloat(i.balance_due || '0'), 0);
@@ -66,18 +126,20 @@ export function InvoicesPage() {
         <Title order={2}>Invoices</Title>
         <Group>
           <Button variant="outline" onClick={() => lateFeesMutation.mutate()} loading={lateFeesMutation.isPending}>Apply Late Fees</Button>
-          <Button leftSection={<IconSend size={16} />} onClick={openBulk}>Generate Monthly Invoices</Button>
+          <Button leftSection={<IconSend size={16} />} onClick={openBulk}>Generate Invoices</Button>
         </Group>
       </Group>
       <Group>
         <Card withBorder p="sm"><Text size="xs" c="dimmed">Total Invoices</Text><Text fw={700}>{invoices.length}</Text></Card>
-        <Card withBorder p="sm"><Text size="xs" c="dimmed">Outstanding</Text><Text fw={700} c="red">{fmt(String(totalOutstanding))}</Text></Card>
+        <Card withBorder p="sm"><Text size="xs" c="dimmed">Outstanding</Text><Text fw={700} c="red">{fmt(totalOutstanding)}</Text></Card>
       </Group>
       <Table striped highlightOnHover>
         <Table.Thead>
           <Table.Tr>
-            <Table.Th>Invoice #</Table.Th><Table.Th>Unit</Table.Th><Table.Th>Date</Table.Th>
-            <Table.Th>Due</Table.Th><Table.Th>Type</Table.Th><Table.Th ta="right">Amount</Table.Th>
+            <Table.Th>Invoice #</Table.Th><Table.Th>Unit</Table.Th><Table.Th>Owner</Table.Th>
+            <Table.Th>Group</Table.Th><Table.Th>Date</Table.Th>
+            <Table.Th>Due</Table.Th><Table.Th>Period</Table.Th>
+            <Table.Th ta="right">Amount</Table.Th>
             <Table.Th ta="right">Paid</Table.Th><Table.Th ta="right">Balance</Table.Th><Table.Th>Status</Table.Th>
           </Table.Tr>
         </Table.Thead>
@@ -86,27 +148,104 @@ export function InvoicesPage() {
             <Table.Tr key={i.id}>
               <Table.Td fw={500}>{i.invoice_number}</Table.Td>
               <Table.Td>{i.unit_number}</Table.Td>
+              <Table.Td>{getLastName(i.owner_name)}</Table.Td>
+              <Table.Td>
+                {i.assessment_group_name ? (
+                  <Badge size="sm" variant="light" color={frequencyColors[i.frequency] || 'gray'}>
+                    {i.assessment_group_name}
+                  </Badge>
+                ) : (
+                  <Badge size="sm" variant="light">{i.invoice_type}</Badge>
+                )}
+              </Table.Td>
               <Table.Td>{new Date(i.invoice_date).toLocaleDateString()}</Table.Td>
               <Table.Td>{new Date(i.due_date).toLocaleDateString()}</Table.Td>
-              <Table.Td><Badge size="sm" variant="light">{i.invoice_type}</Badge></Table.Td>
+              <Table.Td>
+                {i.period_start && i.period_end ? (
+                  <Text size="xs" c="dimmed">
+                    {new Date(i.period_start).toLocaleDateString(undefined, { month: 'short', year: 'numeric' })}
+                    {i.period_start !== i.period_end && (
+                      <> - {new Date(i.period_end).toLocaleDateString(undefined, { month: 'short', year: 'numeric' })}</>
+                    )}
+                  </Text>
+                ) : (
+                  <Text size="xs" c="dimmed">-</Text>
+                )}
+              </Table.Td>
               <Table.Td ta="right" ff="monospace">{fmt(i.amount)}</Table.Td>
               <Table.Td ta="right" ff="monospace">{fmt(i.amount_paid)}</Table.Td>
               <Table.Td ta="right" ff="monospace" fw={500}>{fmt(i.balance_due)}</Table.Td>
               <Table.Td><Badge color={statusColors[i.status] || 'gray'} size="sm">{i.status}</Badge></Table.Td>
             </Table.Tr>
           ))}
-          {invoices.length === 0 && <Table.Tr><Table.Td colSpan={9}><Text ta="center" c="dimmed" py="lg">No invoices yet</Text></Table.Td></Table.Tr>}
+          {invoices.length === 0 && <Table.Tr><Table.Td colSpan={11}><Text ta="center" c="dimmed" py="lg">No invoices yet</Text></Table.Td></Table.Tr>}
         </Table.Tbody>
       </Table>
-      <Modal opened={bulkOpened} onClose={closeBulk} title="Generate Monthly Assessments">
+
+      <Modal opened={bulkOpened} onClose={() => { closeBulk(); setPreview(null); }} title="Generate Assessments" size="lg">
         <form onSubmit={bulkForm.onSubmit((v) => bulkMutation.mutate(v))}>
           <Stack>
             <Group grow>
               <Select label="Month" data={Array.from({length:12},(_,i)=>({value:String(i+1),label:new Date(2026,i).toLocaleString('default',{month:'long'})}))} value={String(bulkForm.values.month)} onChange={(v)=>bulkForm.setFieldValue('month',Number(v))} />
               <NumberInput label="Year" {...bulkForm.getInputProps('year')} />
             </Group>
-            <Text size="sm" c="dimmed">This will generate invoices for all active units based on their monthly assessment amount.</Text>
-            <Button type="submit" loading={bulkMutation.isPending}>Generate Invoices</Button>
+
+            {previewLoading && <Center py="md"><Loader size="sm" /></Center>}
+
+            {preview && !previewLoading && (
+              <Stack gap="xs">
+                <Text size="sm" fw={600}>Billing Preview for {preview.month_name} {preview.year}</Text>
+
+                {preview.groups.map((g) => (
+                  <Card key={g.id} withBorder p="xs" style={{ opacity: g.is_billing_month ? 1 : 0.5 }}>
+                    <Group justify="space-between">
+                      <Group gap="xs">
+                        {g.is_billing_month && g.active_units > 0
+                          ? <IconCheck size={16} color="green" />
+                          : <IconX size={16} color="gray" />
+                        }
+                        <div>
+                          <Group gap={6}>
+                            <Text size="sm" fw={500}>{g.name}</Text>
+                            <Badge size="xs" color={frequencyColors[g.frequency]} variant="light">
+                              {g.frequency}
+                            </Badge>
+                          </Group>
+                          <Text size="xs" c="dimmed">
+                            {g.is_billing_month
+                              ? `${g.active_units} units - ${g.period_description}`
+                              : `Not a billing month for this group`
+                            }
+                          </Text>
+                        </div>
+                      </Group>
+                      {g.is_billing_month && (
+                        <Text size="sm" fw={500} ff="monospace">{fmt(g.total_amount)}</Text>
+                      )}
+                    </Group>
+                  </Card>
+                ))}
+
+                {preview.summary.total_invoices > 0 ? (
+                  <Alert icon={<IconInfoCircle size={16} />} color="blue" variant="light">
+                    Will generate {preview.summary.total_invoices} invoices across{' '}
+                    {preview.summary.total_groups_billing} group(s) totaling {fmt(preview.summary.total_amount)}
+                  </Alert>
+                ) : (
+                  <Alert icon={<IconInfoCircle size={16} />} color="yellow" variant="light">
+                    No assessment groups have billing scheduled for {preview.month_name}. No invoices will be generated.
+                  </Alert>
+                )}
+              </Stack>
+            )}
+
+            <Button
+              type="submit"
+              loading={bulkMutation.isPending}
+              disabled={!preview || preview.summary.total_invoices === 0}
+            >
+              Generate {preview?.summary.total_invoices || 0} Invoices
+            </Button>
           </Stack>
         </form>
       </Modal>

frontend/src/pages/payments/PaymentsPage.tsx

@@ -1,13 +1,13 @@
 import { useState } from 'react';
 import {
   Title, Table, Group, Button, Stack, Text, Badge, Modal,
-  NumberInput, Select, TextInput, Loader, Center,
+  NumberInput, Select, TextInput, Loader, Center, ActionIcon, Tooltip,
 } from '@mantine/core';
 import { DateInput } from '@mantine/dates';
 import { useForm } from '@mantine/form';
 import { useDisclosure } from '@mantine/hooks';
 import { notifications } from '@mantine/notifications';
-import { IconPlus } from '@tabler/icons-react';
+import { IconPlus, IconEdit, IconTrash } from '@tabler/icons-react';
 import { useQuery, useMutation, useQueryClient } from '@tanstack/react-query';
 import api from '../../services/api';
 import { useIsReadOnly } from '../../stores/authStore';
@@ -15,11 +15,13 @@ import { useIsReadOnly } from '../../stores/authStore';
 interface Payment {
   id: string; unit_id: string; unit_number: string; invoice_id: string;
   invoice_number: string; payment_date: string; amount: string;
-  payment_method: string; reference_number: string; status: string;
+  payment_method: string; reference_number: string; status: string; notes: string;
 }
 
 export function PaymentsPage() {
   const [opened, { open, close }] = useDisclosure(false);
+  const [editing, setEditing] = useState<Payment | null>(null);
+  const [deleteConfirm, setDeleteConfirm] = useState<Payment | null>(null);
   const queryClient = useQueryClient();
   const isReadOnly = useIsReadOnly();
 
@@ -39,10 +41,18 @@ export function PaymentsPage() {
   const form = useForm({
     initialValues: {
       invoice_id: '', amount: 0, payment_method: 'check',
-      reference_number: '', payment_date: new Date(),
+      reference_number: '', payment_date: new Date(), notes: '',
     },
   });
 
+  const invalidateAll = () => {
+    queryClient.invalidateQueries({ queryKey: ['payments'] });
+    queryClient.invalidateQueries({ queryKey: ['invoices'] });
+    queryClient.invalidateQueries({ queryKey: ['invoices-unpaid'] });
+    queryClient.invalidateQueries({ queryKey: ['accounts'] });
+    queryClient.invalidateQueries({ queryKey: ['journal-entries'] });
+  };
+
   const createMutation = useMutation({
     mutationFn: (values: any) => {
       const inv = invoices.find((i: any) => i.id === values.invoice_id);
@@ -53,22 +63,88 @@ export function PaymentsPage() {
       });
     },
     onSuccess: () => {
-      queryClient.invalidateQueries({ queryKey: ['payments'] });
-      queryClient.invalidateQueries({ queryKey: ['invoices'] });
-      queryClient.invalidateQueries({ queryKey: ['invoices-unpaid'] });
-      queryClient.invalidateQueries({ queryKey: ['accounts'] });
+      invalidateAll();
       notifications.show({ message: 'Payment recorded', color: 'green' });
-      close(); form.reset();
+      close(); setEditing(null); form.reset();
     },
     onError: (err: any) => { notifications.show({ message: err.response?.data?.message || 'Error', color: 'red' }); },
   });
 
+  const updateMutation = useMutation({
+    mutationFn: (values: any) => {
+      return api.put(`/payments/${editing!.id}`, {
+        payment_date: values.payment_date.toISOString().split('T')[0],
+        amount: values.amount,
+        payment_method: values.payment_method,
+        reference_number: values.reference_number,
+        notes: values.notes,
+      });
+    },
+    onSuccess: () => {
+      invalidateAll();
+      notifications.show({ message: 'Payment updated', color: 'green' });
+      close(); setEditing(null); form.reset();
+    },
+    onError: (err: any) => { notifications.show({ message: err.response?.data?.message || 'Error', color: 'red' }); },
+  });
+
+  const deleteMutation = useMutation({
+    mutationFn: (id: string) => api.delete(`/payments/${id}`),
+    onSuccess: () => {
+      invalidateAll();
+      notifications.show({ message: 'Payment deleted', color: 'orange' });
+      setDeleteConfirm(null);
+      close(); setEditing(null); form.reset();
+    },
+    onError: (err: any) => { notifications.show({ message: err.response?.data?.message || 'Error', color: 'red' }); },
+  });
+
+  const handleEdit = (payment: Payment) => {
+    setEditing(payment);
+    form.setValues({
+      invoice_id: payment.invoice_id || '',
+      amount: parseFloat(payment.amount || '0'),
+      payment_method: payment.payment_method || 'check',
+      reference_number: payment.reference_number || '',
+      payment_date: new Date(payment.payment_date),
+      notes: payment.notes || '',
+    });
+    open();
+  };
+
+  const handleNew = () => {
+    setEditing(null);
+    form.reset();
+    open();
+  };
+
+  const handleSubmit = (values: any) => {
+    if (editing) {
+      updateMutation.mutate(values);
+    } else {
+      createMutation.mutate(values);
+    }
+  };
+
   const fmt = (v: string) => parseFloat(v || '0').toLocaleString('en-US', { style: 'currency', currency: 'USD' });
 
-  const invoiceOptions = invoices.map((i: any) => ({
+  const formatPeriod = (inv: any) => {
+    if (inv.period_start && inv.period_end) {
+      const start = new Date(inv.period_start).toLocaleDateString(undefined, { month: 'short' });
+      const end = new Date(inv.period_end).toLocaleDateString(undefined, { month: 'short', year: 'numeric' });
+      return inv.period_start === inv.period_end ? start : `${start}-${end}`;
+    }
+    return '';
+  };
+
+  const invoiceOptions = invoices.map((i: any) => {
+    const period = formatPeriod(i);
+    const periodStr = period ? ` - ${period}` : '';
+    return {
       value: i.id,
-    label: `${i.invoice_number} - ${i.unit_number || 'Unit'} - Balance: $${parseFloat(i.balance_due || i.amount).toFixed(2)}`,
-  }));
+      label: `${i.invoice_number} - ${i.unit_number || 'Unit'}${periodStr} - Balance: $${parseFloat(i.balance_due || i.amount).toFixed(2)}`,
+    };
+  });
 
   if (isLoading) return <Center h={300}><Loader /></Center>;
 
@@ -76,7 +152,7 @@ export function PaymentsPage() {
     <Stack>
       <Group justify="space-between">
         <Title order={2}>Payments</Title>
-        {!isReadOnly && <Button leftSection={<IconPlus size={16} />} onClick={open}>Record Payment</Button>}
+        {!isReadOnly && <Button leftSection={<IconPlus size={16} />} onClick={handleNew}>Record Payment</Button>}
       </Group>
       <Table striped highlightOnHover>
         <Table.Thead>
@@ -84,6 +160,7 @@ export function PaymentsPage() {
             <Table.Th>Date</Table.Th><Table.Th>Unit</Table.Th><Table.Th>Invoice</Table.Th>
             <Table.Th ta="right">Amount</Table.Th><Table.Th>Method</Table.Th>
             <Table.Th>Reference</Table.Th><Table.Th>Status</Table.Th>
+            {!isReadOnly && <Table.Th></Table.Th>}
           </Table.Tr>
         </Table.Thead>
         <Table.Tbody>
@@ -96,18 +173,34 @@ export function PaymentsPage() {
               <Table.Td><Badge size="sm" variant="light">{p.payment_method}</Badge></Table.Td>
               <Table.Td>{p.reference_number}</Table.Td>
               <Table.Td><Badge color={p.status === 'completed' ? 'green' : 'yellow'} size="sm">{p.status}</Badge></Table.Td>
+              {!isReadOnly && (
+                <Table.Td>
+                  <Tooltip label="Edit payment">
+                    <ActionIcon variant="subtle" onClick={() => handleEdit(p)}>
+                      <IconEdit size={16} />
+                    </ActionIcon>
+                  </Tooltip>
+                </Table.Td>
+              )}
             </Table.Tr>
           ))}
           {payments.length === 0 && (
-            <Table.Tr><Table.Td colSpan={7}><Text ta="center" c="dimmed" py="lg">No payments recorded yet</Text></Table.Td></Table.Tr>
+            <Table.Tr><Table.Td colSpan={isReadOnly ? 7 : 8}><Text ta="center" c="dimmed" py="lg">No payments recorded yet</Text></Table.Td></Table.Tr>
           )}
         </Table.Tbody>
       </Table>
-      <Modal opened={opened} onClose={close} title="Record Payment">
-        <form onSubmit={form.onSubmit((v) => createMutation.mutate(v))}>
+
+      {/* Create / Edit Payment Modal */}
+      <Modal opened={opened} onClose={() => { close(); setEditing(null); form.reset(); }} title={editing ? 'Edit Payment' : 'Record Payment'}>
+        <form onSubmit={form.onSubmit(handleSubmit)}>
           <Stack>
+            {!editing && (
               <Select label="Invoice" required data={invoiceOptions} searchable
                 {...form.getInputProps('invoice_id')} />
+            )}
+            {editing && (
+              <TextInput label="Invoice" value={editing.invoice_number || 'N/A'} disabled />
+            )}
             <DateInput label="Payment Date" required {...form.getInputProps('payment_date')} />
             <NumberInput label="Amount" required prefix="$" decimalScale={2} min={0.01}
               {...form.getInputProps('amount')} />
@@ -118,10 +211,60 @@ export function PaymentsPage() {
             ]} {...form.getInputProps('payment_method')} />
             <TextInput label="Reference Number" placeholder="Check # or transaction ID"
               {...form.getInputProps('reference_number')} />
-            <Button type="submit" loading={createMutation.isPending}>Record Payment</Button>
+            <TextInput label="Notes" placeholder="Optional notes"
+              {...form.getInputProps('notes')} />
+
+            <Group justify="space-between">
+              {editing ? (
+                <>
+                  <Button
+                    variant="outline"
+                    color="red"
+                    leftSection={<IconTrash size={16} />}
+                    onClick={() => setDeleteConfirm(editing)}
+                  >
+                    Delete Payment
+                  </Button>
+                  <Button type="submit" loading={updateMutation.isPending}>
+                    Update Payment
+                  </Button>
+                </>
+              ) : (
+                <Button type="submit" fullWidth loading={createMutation.isPending}>Record Payment</Button>
+              )}
+            </Group>
           </Stack>
         </form>
       </Modal>
+
+      {/* Delete Confirmation Modal */}
+      <Modal
+        opened={!!deleteConfirm}
+        onClose={() => setDeleteConfirm(null)}
+        title="Delete Payment"
+        size="sm"
+      >
+        <Stack>
+          <Text size="sm">
+            Are you sure you want to delete this payment of{' '}
+            <Text span fw={700}>{deleteConfirm ? fmt(deleteConfirm.amount) : ''}</Text>{' '}
+            for unit {deleteConfirm?.unit_number}?
+          </Text>
+          <Text size="xs" c="dimmed">
+            This will also remove the associated journal entry and recalculate the invoice balance.
+          </Text>
+          <Group justify="flex-end">
+            <Button variant="default" onClick={() => setDeleteConfirm(null)}>Cancel</Button>
+            <Button
+              color="red"
+              loading={deleteMutation.isPending}
+              onClick={() => deleteConfirm && deleteMutation.mutate(deleteConfirm.id)}
+            >
+              Delete Payment
+            </Button>
+          </Group>
+        </Stack>
+      </Modal>
     </Stack>
   );
 }

nginx/default.conf

@@ -23,8 +23,21 @@ server {
         proxy_cache_bypass $http_upgrade;
     }
 
-    # AI endpoints now return immediately (async processing in background)
-    # No special timeout needed — kept for documentation purposes
+    # AI recommendation endpoint needs a longer timeout (up to 3 minutes)
+    location /api/investment-planning/recommendations {
+        proxy_pass http://backend;
+        proxy_http_version 1.1;
+        proxy_set_header Upgrade $http_upgrade;
+        proxy_set_header Connection 'upgrade';
+        proxy_set_header Host $host;
+        proxy_set_header X-Real-IP $remote_addr;
+        proxy_set_header X-Forwarded-For $proxy_add_x_forwarded_for;
+        proxy_set_header X-Forwarded-Proto $scheme;
+        proxy_cache_bypass $http_upgrade;
+        proxy_read_timeout 180s;
+        proxy_connect_timeout 10s;
+        proxy_send_timeout 30s;
+    }
 
     # Everything else -> Vite dev server (frontend)
     location / {

nginx/host-production.conf

@@ -74,8 +74,20 @@ server {
         proxy_send_timeout 15s;
     }
 
-    # AI endpoints now return immediately (async processing in background)
-    # No special timeout overrides needed
+    # AI endpoints — longer timeouts (LLM calls can take minutes)
+    location /api/investment-planning/recommendations {
+        proxy_pass http://127.0.0.1:3000;
+        proxy_read_timeout 300s;
+        proxy_connect_timeout 10s;
+        proxy_send_timeout 30s;
+    }
+
+    location /api/health-scores/calculate {
+        proxy_pass http://127.0.0.1:3000;
+        proxy_read_timeout 180s;
+        proxy_connect_timeout 10s;
+        proxy_send_timeout 30s;
+    }
 
     # --- Frontend → React SPA served by nginx (port 3001) ---
     location / {

nginx/production.conf

@@ -40,8 +40,20 @@ server {
         proxy_send_timeout 15s;
     }
 
-    # AI endpoints now return immediately (async processing in background)
-    # No special timeout overrides needed
+    # AI endpoints → longer timeouts
+    location /api/investment-planning/recommendations {
+        proxy_pass http://backend;
+        proxy_read_timeout 180s;
+        proxy_connect_timeout 10s;
+        proxy_send_timeout 30s;
+    }
+
+    location /api/health-scores/calculate {
+        proxy_pass http://backend;
+        proxy_read_timeout 180s;
+        proxy_connect_timeout 10s;
+        proxy_send_timeout 30s;
+    }
 
     # --- Static frontend → built React assets ---
     location / {

nginx/ssl.conf

@@ -60,8 +60,37 @@ server {
         proxy_cache_bypass $http_upgrade;
     }
 
-    # AI endpoints now return immediately (async processing in background)
-    # No special timeout overrides needed
+    # AI recommendation endpoint needs a longer timeout (up to 3 minutes)
+    location /api/investment-planning/recommendations {
+        proxy_pass http://backend;
+        proxy_http_version 1.1;
+        proxy_set_header Upgrade $http_upgrade;
+        proxy_set_header Connection 'upgrade';
+        proxy_set_header Host $host;
+        proxy_set_header X-Real-IP $remote_addr;
+        proxy_set_header X-Forwarded-For $proxy_add_x_forwarded_for;
+        proxy_set_header X-Forwarded-Proto $scheme;
+        proxy_cache_bypass $http_upgrade;
+        proxy_read_timeout 180s;
+        proxy_connect_timeout 10s;
+        proxy_send_timeout 30s;
+    }
+
+    # AI health-score endpoint also needs a longer timeout
+    location /api/health-scores/calculate {
+        proxy_pass http://backend;
+        proxy_http_version 1.1;
+        proxy_set_header Upgrade $http_upgrade;
+        proxy_set_header Connection 'upgrade';
+        proxy_set_header Host $host;
+        proxy_set_header X-Real-IP $remote_addr;
+        proxy_set_header X-Forwarded-For $proxy_add_x_forwarded_for;
+        proxy_set_header X-Forwarded-Proto $scheme;
+        proxy_cache_bypass $http_upgrade;
+        proxy_read_timeout 180s;
+        proxy_connect_timeout 10s;
+        proxy_send_timeout 30s;
+    }
 
     # Everything else -> Vite dev server (frontend)
     location / {