Make sure you don't have any filters set which prevent device > Outlook syncing. In Desktop Manager --> Synchronize --> Configuration --> Configure Synch --> Configure --> Advanced Settings --> Filters. Also in Desktop Manager --> Synchronize --> Configuration --> Configure Synch --> Choose --> Options, make sure you have the correct User Profile selected.
Don't forget the standard "remove the battery for two minutes" and "resend service books" things. I'm way grasping at straws here. Any more hints/clues?