Work requirements mean that I can no longer resist using Microsoft Office (my convenience not a University of Bolton dictate) and the first step of migration was the relatively simple export and import of contacts. 30 minutes of fiddling with export and import options and the only answer I could find was:
1. export vCard from Mac Mail
2. import vCard into GoogleMail
3. export from GoogleMail as csv
4. copy file from OSX environment into Windows environment that now runs on my Mac in the Parallels environment (complete with the startup and shutdown tune all sane people loath
Next will be my calendar, all very depressing on many levels:^(
Why not use Office OSX with Entourage?
Could you not have exported from Address Book as vCards into Outlook?
Pretty sure iCal and Outlook are compatible via the .ics format.