Nano or Classic?
I think classic would be better then nano n fact i also had a classic ipod.
If you're thinking of a Nano because you don't need a lot of storage space, you may as well consider an iPod Touch. Jailbreak it and it becomes a miniature computer.
i have an iPod Touch and i warmly recommend it
If you have a huge library, definitely go for the classic. I love my nano, but that's because I have only about 300 songs. In retrospect, I wish I got a classic so I could put more video content on it.
You have to ask yourself if you have a big library and like videos on the go, or if you just want to listen to a relatively small music library? And of course, do you have the cash to spare?
I would Get the nano because unless you have like 10,000 songs you wont need that mush emty space.
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