I just got mine and had the same problem, couldnt sync with pocket mac. But a friend gave me this tip. Log to blackberry.comand in downloads there is pocketmac4.0 FOR FREE!!! And it works perfect, I sync all my Entourage contacts, tasks, notes, etc into the Pearl!
What I did try, is to upload trhe a micro SD pics, and they wont open, dont know why, but I did get some .doc documents and I was able to attach to emails, its wonderfull!!