i am not sure how you rate the files on the iPod itself but if you go to the playlists on the iPod it will have the most recently played files and then another category is top rated....you can rate the files on iTunes and when you sync the iPod it will automatically add the 5stars to the top of the list
all you do to rate them is when the song is playing tap the middle button twice, one will allow you to change the place in the song, and the second time 5 dots will appear move the whell to back and forth to your desired rating
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