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I can almost guarantee it could be fixed. But he does not have the expertice/experince to do so.

One major issue is he's using a mix of cutting edge (Touch and Office 2007) on a system that is 4 years old (XP and Active sync). One thing in general I find and I'm sure other have if you want to stay cutting edge then you need to be consistent and keep it all cutting edge. Also be prepared for cutting edge problems.

If he went into a store and bought a new Vista and Office 2007 machine I'm sure it would sync up and work fine. But he has an older setup with some history and it takes a bit of experience to clean that all up.

I agree with others. Palm is brain dead. It tend to be stable because of it's lack of features and change. You could make the same argument to have stayed with the older version of office which also probably would have worked.