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1. go to Edit>Preference>iPod and
you need to set it "manually manage songs and playlist"
2. don't have a vpod..so can't help you on this
3. in iTunes, click on the iPod icon (should be under Music Store)
and you'll see all the songs you have in your iPod and click on songs(highlight them). Hit the "Delete" key on your keyboard and it will clear the ones you don't want them in it.
Hope this makesense
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