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First, check out CNET.com for reviews.
Size--if you just want a couple hours of music, the IPod Shuffle is great. Good battery life, really small, holds a G of music for about 80 bucks. If you want something bigger, you can get 4 to 8 Gs in the mid 100s, or you can go for 30 Gs for around 200, depending on brand.
Battery life--the better brands have better battery life. IPod, Zune, Creative, IRiver are the better ones, though there are other brands who make good ones.
Where to get the music--you can upload your CDs to any player. If you want to download, you have to have a service to download from. IPod and Zune have their own sites. Prices are about the same, but there are quirks. IPod won't let you copy music to a different player, for instance. (Though you can cheat this by burning to a CD then ripping the music to another format).
There are other oddities that vary from brand to brand. Some have voice recorders, some you can double as a USB drive for data. It's worth asking a couple of questions, you might actually like one of the bonuses. My Zune, for instance, has an FM receiver. It does not have a clock, which would have come in handy on nighttime jogs.
You can buy a cheaper brand, and wind up with limited download capability or poor batter life.
Anyway, that's it. If you are going for the smaller ones, the Shuffle is the best, but Creative makes a nice one, too. If you are going for the big one, Creative, Zune and Apple are the best. Each has quirks.
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