OK, after a month of struggle, I consulted a Voodoo priest who loaned me a ritual chicken for the day and I seem to have got Contacts and Calendars syncing between Daylite and a Blackberry Pearl without causing London Bridge to fall down on top of my head every time.

So, now I have a sort-of working sync, it's become apparent that PocketMac only seems to sync contacts owned by the User doing the sync. This is a similar question to the one posed earlier today by elagstein, with the problem that PocketMac syncs by Category and not Group, and a Daylite Contact can be only in one Category at a time...

So, my Sales Director can have my Operations Director's phone number on his Blackberry, or my CEO can have it on his, but not both of them.

Short of syncing Daylite with the Apple Address Book and then doing a second sync with the Blackberry from there, are there any other solutions?

You know, that's what I do. Sync DL with Addressbook and then Addressbook with Blackberry. Works without a hitch.

I do overwrite the Blackberry each time though, since a 2 way sync sounds FAR too risky to me.

I've given up on the calendar...