Comment by raggi

This problem space is not small enough to stay within current LLM attention span. A sufficiently good agent setup might be able to help maintain docs somewhat through changes, but organizing them in an approachable way covering all the heuristics spread across so many places and external systems with a huge amount of time and versioning multivariate factors is hugely troublesome for current LLM capabilities. They're better at simpler problems, like typing the code.