FWIW - I gave up on Pocketmac and am running Windows XP/Outlook on my MacBook with absolutely no issues. It syncs perfectly every time.

That said, it is a pain to reboot to run Windows using Boot Camp. I was all set to try Parallel (which allows running Windows XP in a window while you are in OS X) - but discovered that people are having trouble with the USB connection to their Blackberry with that.

So I guess the search for the perfect solution goes on...