I think it's a genuinely tough problem. Keeping documentation up to date is a Sisyphean task - it's great that Amazon has managed to to some extent, but it's hella difficult for small teams.

There's some amount that can be answered by providing a 'beaten path' for people to walk, but a) discoverability is a problem - people often don't know the right keyword to search for to find what they need, and b) people are often subtly off the beaten path, and need some adaptive guidance to their particular situation.

AI answers are great for both of these problems.