I followed portions of the solutions above (in the original posting) and came up with a final solution, that worked for me. It’s true that a calender item has an attachment. Follow these steps (Outlook 2003) to find the offending calender entries. This same solution may work for other areas (tasks, etc) but I used it only because there was a failure on Calender entries.

1) Disconnect your BB from USB
2) Open Outlook
3) Goto Tools|Find|Advanced Find (Ctrl-Shift-F)
4) Set “Look For:” to “Appointments and Meetings”
5) Choose the More Choices tab
6) Check the box for “Only items with: One or more Attachments”
7) Click Find Now
8) Open each email and remove/save off any attachments, pictures (they are considered attachments); I even had a company logo in someones signature show up as an attachment. A horizontal line was even another. Anything that you might think needs to be removed.
9) When you feel you have remove offending attachments, press Esc key
10) Choose “Yes” to save the new entry
11) If any/all attachments have been removed, it will no longer show in the Advanced Find list.
12) When all entries have been processed, connect your BB by USB
13) Everything should be good.

This the end of the original posting.

Following this up, it appears that if there is a large amount of text on any of the Outlook items, this may also cause problems. I haven’t confirmed this myself, but searching for attachments and/or large (>3k) notes will help eliminate some of the crashes.