Get an ipod. I've tried the plain "mp3" thing and it isn't all that great. I had a Toshiba Gigabeat 40 gig, the thing malfunctioned to the point where I just couldn't take it. I took it back and got a 30 gig video ipod. Ipod seems to do a better job of compressing files so they take up less space. What you have to remember when getting one is that iPod has been doing this for a long time, they know how to put out a quality product, that's also reliable.
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