FWIW, I got an iRiver from Woot and I absolutely love it. I love the screen, fm radio, voice recorder, I can load text documents onto it, photos...it's so cool. No problems with it at all.
I hate itunes. BLEH. My daughter has a shuffle, and she can't wait to upgrade.
My other daughter wants an mp3 player for her birthday, so I stuck with iRiver, and found this one on Overstock....
http://www.overstock.com/cgi-bin/d2.cgi?PAGE=PROFRAME&PROD_ID=1802438
I will admit I don't know a whole lot about mp3 players, but I think you can't beat this for $50.00
And regarding "cool factor" my daughter with the shuffle is 16, and she wants the iRiver--not worried about it not being "cool"--a lot of her friends have all sorts of different brands, and my 13 year old is excited about the iRiver, too. I don't think brand matters too terribly much right now. Could be different in your kid's school, though. Kids are weird.