dmbmartin12...Thanks!! Running ActiveSync from the Blackjack fixed my problem.

For others: I had already successfully sync'ed via USB. Had successfully paired via Bluetooth from both the PC and phone, could see on the PC that ActiveSync was using COM5 (from Bluetooth Configuration, Local Services), but ActiveSync would not connect. Running ActiveSync on the phone was the solution.

PS: This link (which I found after making this work) describes the entire process:
MobileViews Blog :: Tips for ActiveSync with Bluetooth

1. Install/setup etc Outlook
2. Install ActiveSync (current version is 4.5)
3. Pair and sync over USB first (MUST do this initially)
4. Install and configure Bluetooth device - note COM port assigned to ActiveSync (look in PC configuration settings eg Local Services)
5. Open up ActiveSync without any device connected to the PC
6. Select your device and open up the Connection Settings window
7. Check the box next to Allow connections and select COM port from step 4.
8. Set Bluetooth on your PC to allow it to be discovered
9. Turn on Bluetooth on your PDA
10. Have your WM device search for other Bluetooth devices and pair with PC
11. Select PDA ActiveSync service and sync via Bluetooth to PC