Context: In my $DAYJOB, we have just started documenting. Its proven useful for humans and AI tools alike. However, code being pushed to prod doesn’t always mean docs are also updated. And we are soon heading towards a place where docs become meaningless.

From people who feel this day-to-day, I want to know: 3. What seems like it will work but doesn’t? (common pitfalls) 4. What solutions have you developed that work? 5. What ends up being the hardest part?

I’ve seen lots of discussion online about this problem, but extremely few concrete approaches.

Or maybe I am approaching this problem fundamentally the wrong way?