Here via a friendslist but um, as long as you have the same account on your Gateway as whatever you've used to transfer onto your iPod, it should transfer the songs you've paid for and downloaded through the iTunes store. Not so sure what to tell you about your music otherwise but my 'paid for' collection that I keep on my PC went right onto my laptop. (Which just meant that I got about 600 Depeche Mode songs and little else. Eheh...)
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