teamwork-vault — Roadmap decisions

Who’s deciding?

Greenlight first · ~$0

1 · R2 orphan-sweeper + lifecycle + customMetadata?

Closes the design’s named “sweep later” gap — a daily Cron job reconciles R2 against D1. No new product surface.

Greenlight nowrecommendedShip customMetadata + 2 lifecycle rules + the Cron sweeper. Defer to next cycleLeave orphans accumulating for now.

Phased

2 · App-level artifact versioning?

R2 has no native versioning — this adds versioned keys + a history read tool, reaped by lifecycle. Opt-in, no hot-path change.

Build phased, after the sweeperrecommendedReuses the customMetadata + lifecycle foundation. DeferRevisit when history is actually requested. Drop itLast-writer-wins is fine; no history needed.

The real upgrade

3 · Vectorize semantic search beside FTS5?

Hybrid keyword + meaning. Adds a 4th write target + Workers AI dependency. The plan is written and ready.

Defer until keyword search missesrecommendedShip the spine first; trigger on real lexical misses. Build nowSemantic recall is worth the added complexity today. DropFTS5 keyword search is enough.

Load-bearing

4 · Vectorize tenant-isolation posture (if #3 isn’t “drop”)

Vectorize is a separate store — the tenant_id invariant doesn’t auto-extend. This is the answer that keeps tenants from leaking.

Shared index + tenant_id metadata + D1 re-checkrecommendedMetadata index created before the first insert; every hit re-verified in D1. One index per tenantHard isolation, but caps + ops overhead. Decide at build time

When needed

5 · Image attachments via Images-on-R2?

Transform straight off the existing R2 bucket — no migration, Free tier (5k/mo). The lightest-touch path.

Enable when first neededrecommendedBuild the seam the moment an artifact needs an image. Build the seam nowGet attachments ready ahead of demand. Not planned

Hold

6 · Cloudflare Stream video hosting?

Hosting recordings vs linking them. URL-ingest needs a direct MP4 — Loom/Zoom share links are HTML pages.

Defer / holdrecommendedPointer model is correct until links start rotting. Pursue nowWe have direct MP4s / want hosted playback. Drop permanently

Next action

7 · What ships in the first commit?

Sets the branch and the first PR scope.

R2 sweeper + lifecycle firstrecommendedBranch feat/r2-versioning-orphan-sweep, ship roadmap 1–2. Bundle items 1–3Include versioning in the first PR. Wait for full sign-offLock every decision before any branch.

Any constraints, timing, or sequencing changes?

Budget windows, a deadline, a tenant rollout, or a reason to reorder — anything that should shape the plan.

Anything else?