I have been using Outlook for as long as I can remember. About two months ago I deleted a trial version of MS Office 2007 because I was using Office 2003 and after I did that I had tons of issues with Office.
I tried everything to fix it and sent hours on forums trying to figure out what was going on. I usually can fix computer issues like this because I am very persistent, but this one frustrated the hell out of me.
Well today I threw in the towel and loaded Thunderbird (free) and it’s add-on for the calendar. It took a few hours to configure everything the way I like it and I gotta say it works just as nice as Outlook. I think I have tested everything.
Only one draw back and it is a major one, I can’t sync everything to my Treo. 
One very cool add-on is the Text Complete. So when I get an email with the same question I alway get - “Do you have any rentals in my town” - with one click I add a simple canned response. Nice!
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1 user responded in this post
I did the same thing a few years ago - got fed up with Outlook crashing all of the time and went to Thunderbird. It has been rock solid. I really like the calendar program addon (sunbird).
Open source rocks.