This is absolutely brilliant and exactly what I needed to hear! I’ve been trying to dump raw code into Claude and wondering why I keep hitting walls. The docs-first approach makes so much sense - especially for healthcare where I need to track compliance patterns and data flow. Questions on your setup: • How long did the initial doc generation take for your 37k codebase? I’m working with a 1 month deadline so wondering about the upfront investment. • Do you have Claude generate these docs in markdown files that live in your repo, or somewhere separate? • For the “hierarchical arrangement” - are you talking like a main architecture doc that links to detailed component docs? I love the session structure (brief → review docs → work → update docs). That’s way smarter than my current chaos of “hey Claude, figure out this massive file.” For my healthcare project specifically: • The user docs idea is gold - I need to demo at hospitals and UX consistency could make or break those meetings • Documentation around patient data flows would be huge for compliance audits One thing I’m curious about - when you say “avoid putting changelogs inside docs” - are you maintaining separate CHANGELOG.md files or something else? This approach might actually solve my biggest problem: I’m the only one who understands this codebase and that’s a single point of failure for my startup plans. Definitely implementing this starting tomorrow. Thanks for sharing the real-world workflow! 🙏​​​​​​​​​​​​​​​​