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I've found the first sync, especially when you have a lot of items you want to combine with your device, works best if you limit.
Instead of having all the items checked from the start, actually do not include any checked items. Then, once the device and PC have set up a partnership, go into Tools, Options... in ActiveSync on the PC and check just one item (I usually do the contacts first since that is the single biggest dataset I'm adding to the PPC) and click on OK. Once it tells you synchronization is complete, you can open Tools, Options... and check another item. It even helps sometimes to uncheck the first item (note, this does not remove the items from your PPC, it simply stops the addition of any new ones. Since it's just been seconds since you just did the synchronization, there are not any new items anyway).
Keep up the process until everything you want has been checked off once. Then you can go back in and recheck everything you want to keep synchronized so new items will be added during future syncs.
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