I may be out of my league here and it may seem like a useless chime, but I had this problem when I was using my HP iPAQ 6515 and Vista with Outlook 2003. The desktop had the DST patch and I thought great that would fix it but turned out that I needed the DST patch for my HP as well. Once I put the patch on the device too, on the next sync it said something to the effect of an error causing everything to need to be resync and when it did it, all was well.
Bizarre enough though, a friend with similar setup using Q9c and Vista with 2007 had his problem resolved when he updated the MDC on his desktop and viola the problem poofed away. Not sure if that was something with the sync conduit or what, but it got fixed. So I am not sure if any of this helps you but I can at least say that I have been there and this solved my problem, don't know why or how and how it translates to you.
good luck though.
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AT&T Motorola Q9h Global 6.1 (no longer my primary device)
HP iPAQ 910c Business Messenger 6.1 Professional (AWESOME!)
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