IME the biggest killers of documentation are: 1) no time set aside to keep it up to date. 2) the tedium of reflecting changes made in one place in 3 others.

IME the biggest killers of documentation are: 1) no time set aside to keep it up to date. 2) the tedium of reflecting changes made in one place in 3 others. 3) the fact that the MVP of a lot of organizations is the go to guy who can answer all the questions while amazing documentation is quickly taken for granted & rarely personalized.