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a: Get an iPod, seriosuly, I've tried the iriver, the zen, the samsung, etc, etc, etc, and really - the iPod is the best.
b: Or, get one that does NOT need any special software to run it, and is simply seen as a mass storage device when you connect it to your computer
if you get a new ipod make sure you have a new(er?) mac os.. my friend bought one of those new style picture ones and had to return it because it wouldn't work on his osx g3 because he doesnt have os tiger or whatever its called.... i thnk he ended up getting one of those $299 refurb jobbies from factory direct and it works fine..
the art director at my studio got the nano already, it's suuuuuper small....personally four gigs is for children and the deaf, I need more storage...but it's sexy as hell...and solid state, which can only work in your favour.
I'm happy with my 20 gig photo....
and no matter what apple haters say, I've yet to see an mp3 player with a better interface than the new ipods....