IPod won't sync my music

Hi there. I'm not exactly technically savy, and I've hit a wall as far as critically thinking is concerned with this issue. So, I cannot figure out what's wrong with my iPod.
I have a 5th Generation iPod and I'm having some problems uploading music. Earlier today, when I plugged in my iPod I realized that some music that I'd formerly purchased at the iTunes store was still on my iPod; I have since purchased the cd, erased the iTunes files from my computer, and downloaded the music from the cd.
An alert popped up saying something to the effect of: "You have purchased music on iPod that have been erased from computer; do you want to download them?" I quickly said yes because I forgot about this music. Then, I uploaded all of the checked items in my iTunes music library, including several playlists. It took a little tinkering (unchecking music that I didn't want to listen to), but I pared down my song selection and crammed the iPod practically to maximum capacity.
Later today, I realized that my iPod now had duplicate copies of the same album, so I tried to delete the purchased music from iTunes, and then update my iPod. But now it won't download that same amount of music??? I've reset, reinstalled, and restored my iPod, but I keep getting notices that it won't hold that same amount of music that it held earlier today.
What might I be leaving out of this process? Is there any way of telling how much I've gone over so I can cut out the appropriate amount of music?
Thanks for any support you guys can give.
David
5th Generation, 60 GB Windows XP

Drag the folder with the music into the open iTunes application window.
(48009)

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