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ITUNES
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I've heard doubletwist from the market works really well for this. I haven't used it personally but every review I have seen says it's one of thee best.
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Try iSyncr. It will sync playlists, album art, play counts. It won't sync any of the "DRM Free iTunes purchases". Use Amazon MP3 if you want to have true DRM free music. It also has a wifi add on to sync over wifi. It works slick.
