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I think it really depends on how you listen and what kind of music you have, whether syncronising via iTunes adds value or not. I don't find it helps me at all. I tend to listen to one album at a time, rather than mixed playlists. I don't buy music online, I rip CDs - the metadata aren't always correct and it messes up automatic playlists. I would love to be able to drag and drop within finder instead of having to use a specific application for this.
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