Comment by starkparker

Not that this solves the hard problem, but there's a simonw post for that: https://simonwillison.net/2018/Jul/28/documentation-unit-tes...

Including screenshots, which a lot of tech writing teams raise as a maintenance burden: https://simonwillison.net/2022/Oct/14/automating-screenshots...

Then there are tools like Doc Detective to inline tests in the docs, making them dependent on each other; if documented steps stop working, the test derived from them fails: https://doc-detective.com/