+1 on downloading WMDC and reinstalling it. I have Windows 7 (64bit) and no problems. Outlook 2010 beta (64bit) didn't work,
but the 32bit version does. But I stopped syncing with outlook, I use gmail's calendar to save my appointments and contact on. This way I don't even have to sync with the laptop unless I want to sync between Quicken and Pocket Quicken.