Beyond that, it's been a thrash. I've done thousands of synchronizations, and I count myself fortunate to run into problems only once monthly or so. I know a bit about translation between diverse data models, so I'm a bit sympathetic.
Synchronization is hard. The original Palm team had more than one genius, though they must have left in later years.
Apple doesn't have the knack. They're quite bad at sync ...
TidBITS Macs & Mac OS X: MobileMe Fails to Launch Well, But Finally LaunchesThe worst of the hard problems in software development is one that executives think is easy to solve -- because they don't know they don't know. These problems tend to get funded with about 1/10 of the necessary resources.
... .Mac synchronization has been the bane of my life for years, with it working erratically, duplicating entries, and working magically without intervention for periods of time. During the MobileMe transition, my laptop Address Book locked up, and despite all efforts won't synchronize at all even when it says it has. (I've deleted its data store, reset the sync, and repaired disk permissions.)
My office desktop Mac restored hundreds of deleted entries, many duplicated, which must have been cached at .Mac, even though they were removed. I went through and reculled my contacts. My iPhone, which is now set and apparently working with live sync, appears to have an out-of-date set of contact entries from after the duplicates were added back in and before I culled...
I think that's what Apple has done with synchronization. Underfunded development by an order of magnitude ...
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