PocketMac seems to work best for folks like me who are using older, pre-Intel Macs. On my PowerMac G4 it has worked beautifully.
Once you get to the G5 Macs you see more problems with PocketMac. For *some* of these folks the solution seems to be to buy Mark/Space's Missing Sync.
Once you get to the Intel-based Macs, both these syncing solutions seem hit-or-miss. Snow Leopard has cured these ills for a lot of users, but others continue to have problems.
BlackBerry Desktop Software for Mac promises to be the savior of us all. Due "sometime in September", it's still MIA. BlackBerry Blog has a good review: BlackBerry Desktop Software: Coming Soon to a Mac Near You! - The Official BlackBerry Blog
For now, it's a waiting game. Familiar territory for us Mac users.