I use Entourage and have had no issues with either the Pearl I had, and the new 8830 I just picked up syncing and transfering the calender, tasks, and contacts with Pocketmac. It has worked every single time without issue. It has never failed to pick it up either.

Contrasted with the legion of issues I have had with the Windows software I am very happy with Pocketmac. I run a PC at work, and I own a MacPro, and the desktop manager has been a complete nighmare on the PC. For simple Syncing I am putting in a vote for the Pocketmac. I just hope BB sticks with it and continues to update it.