Respectfully, once you're getting above $100 USD, you're better off
getting an cheap android phone/tablet.
I didn't catch the first part of this thread, but I agree with you. What I
have to wonder about is what is meant by "compatible with Debian".
I use a Sansa Clip (e.g.
http://www.amazon.com/SanDisk-Sansa-Clip-Player-Black/dp/B002MAPT7U/). It's
~$30, plays MP3, WMA, Ogg Vorbis, and FLAC files, and has a built-in FM radio.
I stuck a 16GB memory card in it to hold more music than I'll ever listen to
in a day.
Like any sane MP3 player or camera or other device, when I plug the Sansa
player into its microUSB cable on my Debian box, a window pops open in KDE and
it's a drag-and-drop operation to copy/delete files to/from the player.
Definitely recommended.