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I bought my wife an iPod nano one time cause we bought into the whole convenience thing. Not smart.
iTunes on pc was a nightmare and still is. It never synched right, then the iPod's display died and it got stuck replaying the same 10 songs over and over.
So even more stupidly I bought another one since we already spend all that time getting our cd collection in iTunes and with all the updates to iTunes and a 3 year newer iPod nano it should be better right.... not really.
But yes we have 2 iPods, grumble.