@Eytan Levy A few things I'd separate before you build anything. Your stated objective is that the company owns the data. Git already gives you that. One company-owned repo, five clones, pull at the start of a session, push at the end. The agent keeps running on each laptop, and the canonical copy lives somewhere the company controls. That satisfies the objective as you wrote it. Questions 2 and 4 assume a hosted surface, and I'd want to hear why you need one before spending on it, because that's the expensive half. On filesystem vs a real DB, I don't think that's the right axis. The useful split is context vs records. Context is anything the model should read whole: client background, engagement history, skills, stage definitions, output logs. Markdown and the filesystem are a good home for that. Records are anything you need to filter, join, audit, or write to concurrently: deal stages, timesheets, invoices, who-changed-what. The filesystem can't do that job, and it fails quietly rather than loudly. You already made this split correctly in the startup project you describe further down, with Postgres for the app data and the ICM folder for the assistant's context. That instinct is right. Worth understanding why, so you can defend it when they ask. The first thing that breaks when you centralize is concurrent writes, not storage. Git's concurrency model is the merge conflict. That holds fine while five people work in separate client folders. It gets ugly the moment two consultants touch the same file, or an agent writes on a schedule while someone has a session open. On access control, the repo boundary is the only lever git gives you, so per-client repos do work. But there's a cost nobody in this thread has named. Once you shard by client, the agent can no longer reason across clients. No precedent, no "how did we handle this at the other account," no pattern reuse. That cross-client recall is a large part of why a second brain beats a folder of notes. Choosing isolation over recall is the real decision in front of you, and it's worth making deliberately rather than inheriting it from what git happens to permit.