You have a lot of capability that isn't wired to pains you keep hitting. The biggest unlock isn't a new tool — it's the scheduler: you keep asking for things to "fire on their own" (morning brief, this scan, runway), and the schedule skill + your existing cloud-routine pattern already do that — they're just under-used. Second biggest: three connectors are dead weight (monday/supabase need auth, circleback is failing) — wire or drop them so the inventory stays honest.
Top move: stop hand-running build_index.py + hand-firing briefings — schedule them. Details in §4.
| Capability | State | Used for what today |
|---|---|---|
| Gmail — business (claude.ai connector) | On | Eden/HOA/Mildred threads, drafts, sends |
| Gmail — personal (gmail-personal, local MCP) | On (new today) | Just wired — ztreitel@ now readable directly (retires the ChatGPT relay) |
| Google Calendar (connector + bot CalendarApp) | On | Now in the morning brief (added this session). Desktop sessions can read it too. |
| Google Drive (connector) | On | Reading MIS/obligations sheets; the future Drive-as-memory migration (39-7) rides on this |
| Cloudflare + Netlify (connectors) | On | ops portal deploy, LevSMS site |
| monday.com (connector) | Needs auth | Nothing — never authenticated. Are you using monday? If no, remove it. |
| Supabase (connector) | Needs auth | Nothing yet — but it's the backend for the 39-5 native/multi-user app idea |
| Circleback (connector) | Failing | Meeting-notes tool — failing to connect. Fix (useful for Eden mediation calls) or drop. |
| schedule skill (cloud cron routines) | Under-used | 2 routines live (Weekly Review Sun, Mon-Eve plan). Could fire the morning brief, this scan, runway. |
| loop skill (interval re-run) | Unused | Polling/iterating tasks in-session |
| hookify skill (behavior rules) | Unused | Could codify recurring traps so they never bite twice (see §5) |
| claude-md-improver / revise-claude-md | Unused | Your CLAUDE.md + CONTEXT are stale (38-K2/K3) — these fix exactly that |
| Local scripts | On | now.ps1 (date), notify.ps1 (SMS), inbox.ps1 (bot read/write), setup-gmail-personal-mcp.ps1 |
| hookstreet-skills (your own) | On | session-operator, command-inbox-engine, mis-daily-report, underwriting-method, +10 more |
Recurring pains pulled from SCOPE_BACKLOG (sessions 36-39) + this session:
| Recurring pain | Evidence |
|---|---|
| Things don't fire on their own — briefings, scans, reviews need you (or me) to hand-trigger | Morning spine "paper-only" gap; you've said "I want it to self-learn and offer things"; 38-K7 |
Portal index lags — new outputs deploy but don't show until build_index.py is hand-run | 38-K6; I ran it manually ~6× this week |
Self-capture broken — .remember/now.md writes empty | 38-K5; 38-K7 |
Same setup traps bite twice — .json.json filename, em-dash breaking PowerShell, clasp --force | this session (all 3 cost minutes) |
| Docs go stale — CLAUDE.md / CONTEXT lag sessions behind | 38-K2, 38-K3 |
| Money picture isn't live — cash-IN vs OUT not wired into the brief | 39-6 runway layer |
| Two inboxes, one assistant | SOLVED today (gmail-personal) |
Honest inventory means cutting noise. Three connectors do nothing:
You own the schedule skill + an existing cloud-routine pattern (Weekly Review, Mon-Eve plan already fire). The morning brief now has rich content but still depends on a 6:48 AM Apps Script trigger; this scan, the runway check, and the KB-health-check all run only when triggered by hand. Wire them as cloud routines.
Stop hand-running build_index.py. Make it a git pre-push hook (or a Cloudflare build step) so outputs/index.html regenerates from the folder automatically every push. The portal never lags again.
Three traps cost minutes this session (.json.json, em-dash-breaks-PowerShell, clasp push needing --force). The hookify skill turns "mistakes I made" into guardrails that auto-warn next time. Codify these three + the "write dedup-date AFTER send" MIS rule.
.remember writer.remember/now.md writes empty (38-K5) — the auto session-state capture is broken, which is half of why there's "no self-learning loop." Fix the writer so each session leaves a real breadcrumb.
claude-md-improver on the stale docsCLAUDE.md (Session 37 stale) + CONTEXT.md (Session 36 + self-noted gaps) lag reality. You have a skill built exactly for this. Run it as part of the monthly cadence.
Saved as docs/CAPABILITY_SCAN.md — a repeatable procedure any Claude session can run: inventory MCPs/skills/scripts → mine SCOPE_BACKLOG + .remember + recent outputs for friction → match capability to pain → rank → report. Cadence options (your pick):
schedule skill (it's a recurring autonomous agent, so I'm flagging it as a say-go item — it fires + costs on its own).