> If not, note every single place they fail, address each one, and repeat with a new user.

Might not this loop be invoking Goodhart's Law?

What is "address each one": are we just changing that document, or are we (also) changing something in the system that the document is about?

If no newbie has any problem following the document, is that still a good document for non-newbies?

If no newbie has any problem with the system that the document is about, are there any downsides?