I have also had this problem, but found out it had to do with google calendar invitations that where added to my outlook calendar. I have been able to recreate the problem many times. If you are connecting to your gmail via MS Outlook and someone sends you a calendar entry from google calendar, Outlook handles this fine, but when you go to sync your blackberry Desktop Manager crashes. Desktop Manager will continue to crash until you remove all Outlook calendar entries from google.
Let me know if anyone has found a work around for this problem. I know my post is specific to Outlook entries from google calendar, which have attachments. I relizes this is most likely a bigger issue, and not a specific problem with the google calendar format.