ITunes 10 bug? First track of albums won't sync to iPod

Really weird behavior I've noticed with iTunes 10 - when I add a new album to my iTunes library, and then sync my iPod, the first track of the album isn't copied over. Sync the iPod a second time, and the missing track is copied over.
I've noticed this on two separate occasions, with two different albums. One was from the iTunes Store and the other wasn't.
Any ideas? I have an old iPod Photo, but never noticed this behavior before. Started sometime after iTunes 10 came out.

Quit iTunes. Delete a file named com.apple.usbmuxd.plist~orig, located in the User Name>System>Library>LaunchDaemons. Go to User Name>Library>Preferences. Locate the file com.apple.iTunes.plist. Move that file to the desktop. Reopen iTunes and it will be like the first time you click on it but your file is not going to be gone. It seems like a support file issue.

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