I would love a doc framework that was structured in a way to expose that and shame bad design. "How to FOO because we couldn't manage to make it easy for you" and "3 ways to work around our BAR" would be wonderful help topics. Topics indexed by known problem with the software. Etc.
Diátaxis could be used that way, but is not necessarily a forcing function.
And as far as user-friendly, I'm pretty sure users would appreciate the honesty.