Jason asks for advice on self-contained non-bloated calendaring programs that aren't Outlook. I've been meaning to ask this question for years. Some answers include Task Plus, Calendarscope, Time & Chaos, Corporate Time, several votes for Palm Desktop of all things, web-server-based phpGroupWare (with possible future Mozilla Calendar integration, though Mozilla Calendar itself is perhaps too buggy to use at the moment), and even Yahoo! Calendar which has notification support in Yahoo! Messenger (I think).
I'd just use Outlook to check email and use the calendar features if I could figure out how to keep my filtered mail folders in order. The solution probably involves recreating all my Pine filters as procmail recipes, with perhaps some magic to make sure my folders stay intact with IMAP. Not sure if it's worth it.