I had the same issue as well... (Outlook 2007 and Windows XP SP2)
What worked for me was uninstalling HTC Sync AND the HTC Drivers
Reinstalled HTC Sync with phone unplugged.
Following the posts above, it still didn't work right away either (after plugging the phone in and waiting a few seconds), but once I select the HTC Sync on the phone, it executed the sync manager which allowed me to set up everything manually, it did however, make duplicate entries on some reoccuring appointments/meetings due to the ones in my phone were newer than the ones in Outlook.
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