IPod Classic - AutoSync stops copying music midway, but does not freeze.

I have a brand new 160 GB Classic. When I connect it to my Powerbook, it begins the normal process of auto-syncing my library. I have a total of just over 5000 songs; When it gets to about 3200, it stops, and says Sync is complete. I press "Sync" again, and it starts where it left off, but then stops again at around 4800 songs. I've gone thru this several times, and am now 4 songs away from getting a "complete" sync (where my entire library will finally be copied onto my iPod).
What's causing the iPod to think that it's already copied everything when there's still more stuff it needs to copy?

Dandy.
Well, for anyone looking at this, I may have figured it out. I had a total of 5366 songs in iTunes; after numerous clicks of the "Sync" button, I was able to get 5365 of them on to the iPod. However, even in Manual mode, I was not able to get the one remaining song to transfer. It took me a good while, but I tracked down which song it was. For whatever reason, it would not copy, even though it was a song ripped from one of my own CD's, and it played fine on my Powerbook and my 4th Gen iPod. I deleted the song, re-ripped it, and it transferred fine. My assumption is that iTunes stopped transferring music once it came to this track in the library.
If that doesn't sound like the case, someone please reply.

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