Honestly I would consider a Dell Jukebox.
I am not sure about the IPOD, but I got so sick and tired of the digital rights managers on so many devices. I am a long time supporter of the Sony Mini-disc, but the whole convert your MP3 to ATRAC, check in—check out thing was just ridiculous. Same thing for the two Panasonic players I have.
I got the Dell Jukebox as a gift, and you just click and drag MP3’s from the HD to the player ... done. No re-converting to proprietary format (which takes time), or having to deal with the crazy restaints of the DRM software.