I can't help you with why it's not working, but can tell you that it should. However, I offer a couple observations regarding syncing the Now Calendar using PocketMac.

In my experience, the two way sync is problematic at best. Using it, I've ended up with duplicate entries if , for instance, I change the time of an appointment on the Blackberry Pearl. The safest approach for me is to make all changed in NUTD and always overwrite the Blackberry. In addition, DO NOT select the PocketMac/Blackberry feature of keeping only the last 60 days or so or appointments. Doing so, and then attempting a two way sync will wipe out the older data in NUTD also. Lastly, I don't find the Tasks function on the Blackberry to be very useful, so don't sync Now's To-Dos at all. The few times I've tried I've ended up with random hangs of PocketMac.

In the end, I'm not all that happy with PocketMac; however, it does work pretty well if you just use it to "push" data to the the Blackberry.