Restructure chat service, web routes, and add test suite

Split monolithic chat service into modular structure with Matrix client
support, extract web server into per-resource route modules, introduce
bootstrap/main-loop separation, and add comprehensive vitest coverage
across services, repositories, and utilities. Adds project docs and
CLAUDE.md agent instructions.

src/database/client.ts

@@ -57,12 +57,23 @@ export function runMigrations(db: Database.Database): void {
       created_at INTEGER NOT NULL
     );
 
+    CREATE TABLE IF NOT EXISTS activity_log (
+      id INTEGER PRIMARY KEY AUTOINCREMENT,
+      timestamp INTEGER NOT NULL,
+      type TEXT NOT NULL,
+      message TEXT NOT NULL,
+      recipient TEXT,
+      image_url TEXT
+    );
+
     CREATE INDEX IF NOT EXISTS idx_posts_subreddit
       ON processed_posts(subreddit);
     CREATE INDEX IF NOT EXISTS idx_posts_processed_at
       ON processed_posts(processed_at);
     CREATE INDEX IF NOT EXISTS idx_posts_message_sent
       ON processed_posts(message_sent);
+    CREATE INDEX IF NOT EXISTS idx_activity_log_timestamp
+      ON activity_log(timestamp);
   `);
 
   // Add new columns to existing tables (safe to run multiple times)

src/database/repositories.ts

@@ -26,6 +26,7 @@ export interface SentMessageRecord {
   subreddit?: string;
   postTitle?: string;
   postImageUrl?: string;
+  postImageAnalysis?: string;
 }
 
 export interface SuccessfulMessageRecord {
@@ -60,6 +61,80 @@ export interface DailyTrend {
   responseRate: number;
 }
 
+export interface ActivityLogRecord {
+  timestamp: number;
+  type: string;
+  message: string;
+  recipient: string | null;
+  imageUrl: string | null;
+}
+
+export class ActivityLogRepository {
+  private insertStmt: Database.Statement;
+  private getRecentStmt: Database.Statement;
+  private pruneStmt: Database.Statement;
+  private countSentSkippedStmt: Database.Statement;
+
+  constructor(private db: Database.Database) {
+    this.insertStmt = db.prepare(`
+      INSERT INTO activity_log (timestamp, type, message, recipient, image_url)
+      VALUES (?, ?, ?, ?, ?)
+    `);
+
+    this.getRecentStmt = db.prepare(`
+      SELECT timestamp, type, message, recipient, image_url
+      FROM activity_log
+      ORDER BY id DESC
+      LIMIT ?
+    `);
+
+    this.pruneStmt = db.prepare(`
+      DELETE FROM activity_log
+      WHERE id NOT IN (SELECT id FROM activity_log ORDER BY id DESC LIMIT ?)
+    `);
+
+    this.countSentSkippedStmt = db.prepare(`
+      SELECT COUNT(*) AS count FROM activity_log WHERE type IN ('sent', 'skipped')
+    `);
+  }
+
+  insert(item: {
+    timestamp: number;
+    type: string;
+    message: string;
+    recipient?: string;
+    imageUrl?: string;
+  }): void {
+    this.insertStmt.run(
+      item.timestamp,
+      item.type,
+      item.message,
+      item.recipient ?? null,
+      item.imageUrl ?? null,
+    );
+  }
+
+  getRecent(limit: number): ActivityLogRecord[] {
+    const rows = this.getRecentStmt.all(limit) as Record<string, unknown>[];
+    return rows.map((row) => ({
+      timestamp: row.timestamp as number,
+      type: row.type as string,
+      message: row.message as string,
+      recipient: (row.recipient as string) ?? null,
+      imageUrl: (row.image_url as string) ?? null,
+    }));
+  }
+
+  prune(keep: number): void {
+    this.pruneStmt.run(keep);
+  }
+
+  countSentSkipped(): number {
+    const row = this.countSentSkippedStmt.get() as { count: number };
+    return row.count;
+  }
+}
+
 export class PostsRepository {
   private insertStmt: Database.Statement;
   private existsStmt: Database.Statement;
@@ -166,6 +241,7 @@ export class PostsRepository {
 export class MessagesRepository {
   private insertStmt: Database.Statement;
   private getByPostIdStmt: Database.Statement;
+  private getLatestByRecipientStmt: Database.Statement;
   private getRecentStmt: Database.Statement;
   private getUncheckedStmt: Database.Statement;
   private markResponseStmt: Database.Statement;
@@ -180,8 +256,19 @@ export class MessagesRepository {
 
     this.getByPostIdStmt = db.prepare(`SELECT * FROM sent_messages WHERE post_id = ?`);
 
+    this.getLatestByRecipientStmt = db.prepare(`
+      SELECT sm.*, pp.subreddit, pp.title AS post_title, pp.image_url AS post_image_url,
+        pp.image_analysis AS post_image_analysis
+      FROM sent_messages sm
+      LEFT JOIN processed_posts pp ON sm.post_id = pp.id
+      WHERE sm.recipient = ? COLLATE NOCASE
+      ORDER BY sm.sent_at DESC
+      LIMIT 1
+    `);
+
     this.getRecentStmt = db.prepare(`
-      SELECT sm.*, pp.subreddit, pp.title AS post_title, pp.image_url AS post_image_url
+      SELECT sm.*, pp.subreddit, pp.title AS post_title, pp.image_url AS post_image_url,
+        pp.image_analysis AS post_image_analysis
       FROM sent_messages sm
       LEFT JOIN processed_posts pp ON sm.post_id = pp.id
       ORDER BY sm.sent_at DESC
@@ -235,6 +322,12 @@ export class MessagesRepository {
     return this.mapRow(row);
   }
 
+  getLatestByRecipient(recipient: string): SentMessageRecord | undefined {
+    const row = this.getLatestByRecipientStmt.get(recipient) as Record<string, unknown> | undefined;
+    if (!row) return undefined;
+    return this.mapRow(row);
+  }
+
   getRecent(limit: number = 10): SentMessageRecord[] {
     const rows = this.getRecentStmt.all(limit) as Record<string, unknown>[];
     return rows.map((row) => this.mapRow(row));
@@ -340,6 +433,7 @@ export class MessagesRepository {
       subreddit: (row.subreddit as string) || undefined,
       postTitle: (row.post_title as string) || undefined,
       postImageUrl: (row.post_image_url as string) || undefined,
+      postImageAnalysis: (row.post_image_analysis as string) || undefined,
     };
   }
 }
@@ -358,7 +452,7 @@ export class SuccessfulMessagesRepository {
     `);
 
     this.getRecentStmt = db.prepare(`
-      SELECT * FROM successful_messages ORDER BY created_at DESC LIMIT ?
+      SELECT * FROM successful_messages ORDER BY created_at DESC, id DESC LIMIT ?
     `);
 
     // Get examples prioritizing same subreddit, then falling back to others