Update: Backed up and wiped device. Deleted the address book with only 11 entries and restored, but the device was still showing multiple address books, one is "Desktop" the other is "Unknown". Desktop address book still showing Wireless Sync = Not avail.
Set "Unkown" address book to Wireless Sync = No and pulled batty on device.
On reboot, there is now only the "Desktop" address book, Wireless Sync = Yes
Outlook Contacts have not updated.
<Insert clever remarks here>