Tyler, were you ever able to find a solution to your sync issue? I am not familiar with the Imagio, but from a bit of reading on the Verizon Web site, I found a lot of discussion of the Wireless Sync application, which is a sync alternative Verizon offers. Does the Imagio come with this application under Programs or All Programs? You should be able to tap Start to see all your programs.
If it's there, you may need to launch it, then go to Menu > Settings > ActiveSync and enable ActiveSync for the desktop PC.
But again, I'm not looking at the phone, and this may not be relevant for you at all. Sorry I can't offer more help!