Jwheeles: What messages are logged to the Console when you try to sync? (You can check by running the Console application in /Applications/Utilities.) Please send those log messages to
omnifocus@omnigroup.com and carbon-copy me at
kc@omnigroup.com.
debz0r: Thanks for those additional details! What shows up on your Console when you synchronize? (Please send log messages to
omnifocus@omnigroup.com and carbon-copy me at
kc@omnigroup.com.) What happens if you create a new calendar in iCal and synchronize a context with it? Do any of the items show up in that new calendar? I should note that iCal's search window doesn't search all the calendars, only the active ones (the ones with the corresponding checkbox checked in the left sidebar).