Had all sorts of issues much like this;
Did you have a previous BB ?
If so, you will need to completely remove, not just ininstall, Pocketmac, ie remove all the Pocketmac folders from user/Library etc.. and reinstall
The USB cable with the Pearl also seems specific as the 8700 USB cable doesn't provide connectivity
There are a couple of other glitches on Contacts as well, all contacts must have some Category assignment, a default of "none" causes an error
And entourage must be running
Hope that helps a little