D.inkie - a couple of observations... 1) None of the various iPods have organic encoding ability - all require a PC for encoding. 2) "PLAY LIST HIERARCHY - Enables large volumes of music management by Genre/Artist/Title etc." is the same claim that was made for the CHD1000; it does not necessarily mean that the player indexes files by the ID3 tag info - although the MusicMatch software (not supplied with the second-generation CHD500, BTW) is capable of using ID3 tagging as the source for playlist info/track tagging.