Try removing all external devices except your iPod and syncing again. You can also reset your iPod (by pressing the menu button and the center button until the screen goes black and the Apple logo ...

A growing number of MacFixIt readers are reporting an issue where tracks purchased through the iTunes Music Store do not automatically transfer to an iPod during the on-connect synchronization process ...

I don't know jack about working w/ iPods but I've got a customer who needed some help migrating an existing Hp 40GB iPod from a dead Windows system to a his new XP Pro Sp2 Latitude D620.<BR><BR> * ...