On a point 5, never underestimate the amount of labor someone is willing to undergo in order not to learn something. Educators everywhere share your struggle!
You should also take into consideration that reading docs takes time. If a different designer (marketing guy) is supposed to do a simple 30m task (draft that Merry Christmas popup real quick), they probably won't get those extra 5 hours to read the docs
And after those 5 hours you spend another 5 hours beating your head against the wall until you finally realize the docs are out of date.
Stale docs are worse than no docs. IME (at non-FAANG, non-tech darling companies) docs *always* go stale pretty quickly. No one wants to take on the thankless, unbudgeted task of keeping the docs up-to-date, or browbeating all the other devs to update the docs when they make changes.
The only docs I push for are stuff like swagger where the documentation is also living code. Otherwise I say just put it in the readme, and every repo has a clear owner responsible for keeping that readme up-to-date as necessary.
I think this is an expectation thing. People expect to be able to figure it out in time x. They expect they'd have to use y time to find the solution in the docs. And people will most often estimate that x <<< y, having been burned by bad documentation before. People will often be disappointed that their search through the docs didn't get them any answers and most people will have strong memories of "figuring it out eventually" by throwing spaghetti at the wall long enough.
