In Windows world, syncing your Pocket PC / Windows Mobile device is rather easy, you can use ActiveSync or Windows Mobile Device Center and off you go. However, on a Mac, this may be trivial.
MarkSpace has been filling this void with Missing Sync for Windows Mobile for some time, but it is $40 to buy.
I just found out there is another kid in town, and it is free. Sync Mate for Mac is currently in beta. You can read more about it at:
Eltima Blog
And while at it grab a copy. I haven’t tried it yet, but it is very