Jamie,

About approaching a boss (or anyone for that matter) on a sensitive subject, I highly recommend this book. I just finished it and it was an answer to prayer for me and it sounds like it could help you deal with your boss.

Crucial Confrontations: Tooks for Resolving Broken Promises, Violated Expectations, and Bad Behavior

Authors: Kerry Patterson, Joseph Grenny, Ron McMillan, and Al Switzler.

It's well written, highly readable.