Can't sync BB with OS X 10.5.4 using iCal or Entourage

Hello!
I've been a Blackberry user for a couple of years and have recently switched from Microsoft Outlook to the Apple. I cannot get PocketMac sync to work properly with either iCal or Entourage. I can sync from the Blackberry to the Apple, so my device is recognized, but not the other way around (either using the merge or 'overwrite device' options). Pocketmac acts as though sync is occurring and displays no errors, but no changes are made to the Blackberry handheld. Entering everything only on the handheld is a major pain!
I've tried syncing to iCal and to Entourage individually and neither seems to perform sync BACK to the handheld.
PocketMac suggests running a clean sync utility or rebuilding the Entourage database, both of which I have done to no avail.
Does anyone else have suggestions for syncing with an Apple, short of purchasing an iPhone?
HELP and THANKS! K.

I currently do this with an iMac along with EyeTV and Time Machine. There used to be limitations with older versions of iLife, but I think it was just the installer being difficult, but those are no longer present in the shipping versions of Server and iLife. Time Machine might be considered an issue because by default, Time Machine doesn't back up a few directories which would not have any bearing on normal OS X, but is a bit daunting with OS X Server, specifically /var/spool/ as this is where all mail is stored. You can override this behavior by modifying the Exclusion file in /System/ which some would consider a no no.

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