I run a home server with somewhere around 100 small projects on it, and I do the work with AI agents, mostly through Claude Code. For a long time the agents kept guessing: What port is this service on, what's the path to that config, is this the name of the real thing or the name of the thing from three rewrites ago. They would guess, act on the guess, and sometimes the guess was wrong and something broke.
The instinct is to write it all down which I tried. Documentation is outdated the moment reality moves and reality moves constantly on a box like this, because I'm the one moving it, on a whim, at whatever hour I feel like it. A doc that says a service runs a certain way is only true until I change it and forget to update the doc, which is most of the time. Well it is until I remember to update documentation, but I never remember all of it. So the agents would read a doc, trust it, and be wrong anyway.