> A disorganized pile of classes and methods in code may work – a pile of work of words and paragraphs won’t work. Writing HAS to be clear if it is to be of any use. Code will be accepted (to some extent) as long as it does its job.
This suggests to me that the problem with writing documentation isn't that writing in itself is hard. It is that it is hard to write clearly about badly organised code. So the average programmer can get his disorganised pile to compile and pass the tests, but he can't clearly articulate, in speech or in writing, its organisation.
It's similar to the problem of naming things. If it is hard to find a clear and precise name for a class, it is usually because the purpose of the class isn't clear and precise.
So my suggestion is to write the documentation in advance. If the organisation of the code is very hard to express in plain English, then it is because the organisation of the code isn't very well thought through in the first place, and should therefore be worked on some more. And that is easier to do before a lot of code is written already.