Itunes only syncs a few songs at a time

I just updated to the latest version of itunes on my windows xp machine. It used to update my ipod without any problems, but I haven't synced in several months. Now, when I plug my ipod in and open itunes, it starts syncing but then stops at some arbitrary number of songs (fewer than 100). This is a big problem since I have thousands of songs to sync onto my ipod (I reset it, so it's empty).
What's going on? I went through the preferences with a fine tooth comb and didn't see anything out of the ordinary.
Thanks.

Ideally, I'd like to sync to my gmail account. It syncs a few contacts without a problem, but that's about 15 out of around 200. I'm not sure why it won't sync the rest properly

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