What is the difference between "don't transfer" and "transfer"?

After upgrading a song to iTunes Plus, I will sync my iPod Nano. Upon insertion of the USB cord I will get a message that reads something like this: There are songs on Susan's IPod Nano that are not in your Music Library, "transfer" or "don't transfer". Then it claims if you click "don't transfer" you will lose something on your iPod. But if you click "transfer" you get a duplicate right back into your Library; the 128kbts version, and the 256kpts version. My question is, am I correct in clicking "don't transfer"? I don't want duplicates anywhere! And what remains on he iPod, the 256kbt version or what? Yesterday, I called Tech Support, and the gentleman at the other end had absolutely NO CLUE what I was talking about! First he told me "transfer", then he told me "don't transfer". Can someone who has been through this help? Many thanks.

Hmmm, good question. If you use auto updating with your iPod, my gut feeling is that the old version that is in the iPod but NOT in the iTunes library anymore will be wiped from the iPod if you pick don't transfer.
Basically when you auto update, iTunes matches the contents of the iPod to that of iTunes based on whatever rules you are using (updating all or updating specific playlists). If it isn't in iTunes then it gets removed from the iPod. When you plug in the iPod, if iTunes "sees" a purchased track on the iPod that is not in the library, before it goes ahead and wiped it off the iPod, it gives you the opportunity to first save it to your library. If you say DON'T transfer it, then I assume (but I don't know for sure) that iTunes then goes about its normal updating routine which would remove the track from the iPod since it isn't in the library.
Patrick

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