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HP play is pretty bad, at least on the mac.
as others said, try media monkey, missing sync, or patches for iTunes.
if only Apple didn't go out of their way to make all itunes users upgrade itunes to prevent apple itunes customers from using their devices to play music they purchased from itunes... Apple would never exploit a monopoly in one area, like a music store, to expand in another, like mp3 players, because that kind of activity would be obviously illegal...
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