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I don't care how amazing that Apple, RCA, iRiver et al think that their "jukebox" software is - every app I've ever seen is irritating and detracts from my using the device to listen to music. There's also the irritating tendency to embed dumb DRM into such apps and deliberately limit the use of the device as a removable harddrive because of the record/movie business's insane paranoia about piracy.
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Have you used iTunes? My iPod shows up on my desktop as a Firewire drive that I can drag-n-drop files to. The folder the music is hidden is is hidden from direct access by me to keep the RIAA happy, but that's easy enough to change with a variety of programs which I could keep stored on my iPod.
As far as iTunes goes, plug in my iPod and a symbiotic relationship is formed. As the music on my computer changes, the iPod is updated accordingly. All automagically. As I listen to songs on the iPod, or rate them (1 to 5 stars) that data is also transferred back to the computer. The iPod, instead of feeling like an MP3 player, feels like an extension of iTunes. iTunes to go, so to speak.