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I vote for the iPod option. Go to ebay and get a "classic" iPod with 120 or 160GB of space. More than enough room to keep all but the largest music collection with you.

If your library is not too big, consider one of the smaller iPod touch's. Nice thing about this is that it has wifi. If you park your car within range of your computer at home (as I do - in my garage), you can actually sync it up without ever removing it from the vehicle. As I listen to a lot of podcasts, and use a 160gb Classic iPod, I have to remove the iPod and attach it to the computer to sync. Not a big deal but certainly less convenient than the wifi option.
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