How much storage you will need, wanted features, and file formats your library uses would be very helpful.
quick reccomendation: I'd suggest a Zune over an Ipod classic any day
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Ultra Portable: High BR MP3 > Creative Zen Sleek > Jbuds J2
Main Portable: High BR MP3 > Creative Zen Sleek > Sony MDR-V7
Dorm rig: Sony portable CD player > Some ancient Yamaha reciever > Sony MDR-V7
Someday, the Pandora will launch, and I can ditch the Zen. And maybe an amp. and a sansa clip for my ultraportable. and....
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