Calendar sync crashes iPod

I'm trying to sync iCal to my 5th gen, 80 GB iPod. I'm running OS X 10.4. 8 with all avaialble updates installed and iTunes 7.02.
I can happily sync videos, songs, games, address book to my iPod but whenever I enable calendar sync the iPod goes into a rebooting loop that is very hard to get out of (while rebooting I press Play and select to go to some special iPod mode and then I have to restore the iPod).
Is this is a known problem and is there a solution?
Thansk
5th gen 80GB   Mac OS X (10.4.8)  

This is meant with a bit of humor in the first part of my response to illustrate why polls asking for people not having a problem can be inaccurate here. Then I will get into some suggestions that are more techical in nature.
If you walk to the waiting room at your local hospital's emergency room, and ask is there anybody here who is waiting to see the Doctors who is not sick or injured, please speak up. If everything was working, would you be here to post?
If you turn off Outlook Syncing, and turn it back on, do you get the Windows security screen? It might pop up under the iTunes 7 window. There is a screenshot of the window I am referring to here:
http://docs.info.apple.com/article.html?artnum=302268

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