This is so funny -- and so sad -- because this is EXACTLY what's happening in my small company right now.
* Our UIs are confusing and inconsistent across the family of products
* The docs were written by geeks, not for "mere mortals" and have never been kept up to date
* Online support database? What's that?
* The product development manager and the CEO are in their "special places"
Could it be The Dilbert Principle: A Cubicle's-Eye View of Bosses, Meetings, Management Fads & Other Workplace Afflictions (Paperback) by Scott Adams 1990. My copy is old and on a shelf in the basement.
You know, there's a very good book I've read which is about something very similar to the Peter Principle. It's called the Dilbert Principle, you should try it. I can't remember who it's by though... :)