People referring you to Scott Ambler's essays are right on. In a recent email newsletter he talked about the right reasons to document - to communicate to external groups, to communicate clearly to peers, to help yourself figure things out, etc - and the wrong reasons. Good things to check yourself against now & then.
Boundary & controller objects. Start with them there on your first cut. Depending on your framework and platform, controllers may go away as other objects take on the responsibilities. If they're not interesting after the third diagram, ditch em.
The ONE CLASS DIAGRAM is pretty silly. When I started using Rational
Rose it was a neat epiphany to understand it held one MODEL but let you draw many DIAGRAMS with any subset of the model you needed to get some idea across. The difference between model & diagram might help you talk this through with the mgr. If he's seriously clueless about OOAD, try to enlighten him or brush up your resume.
Sequence diagram per external stimulus. Probably overkill, but a useful thing to think about. What I usually find is that the first one is very interesting, the second one is real similar, and most of the rest are (yawn) more of the same. You'll find yourself working out an architecture that explains the general case, and only the exceptional cases are interesting after that. I'm on a new system right now with an unfamiliar vendor architecture, so we're hammering out a notation to show multiple interactions in one diagram, trying to see what's important and what's not. We've done that first really interesting one so far.
I'm sure by next month these diagrams will be much briefer and we'll have a vocabulary of standard bits that make most pictures unnecessary.
Collaboration diagrams - break em up when they get too messy to read.
Try to relax, adapt your design techniques to the situation, don't feel locked into any "right" set of artifacts or processes. I hope you can have fun at this in your environment.