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In my experience, the wireless sync doesn't like to transfer large amounts of information. Whenever I've done a hard reset, I've had to transfer the contacts (which is several hundred records) via the cable connection. I don't keep a lot of appointments in my calendar, but if you do, this might apply to that as well. Once the bulk of information is transered, it can handle the day-to-day changes.
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-Ike-
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