Use an ipod, iriver, cowon, or archos HD or flash player. Put rockbox on it. Use it with any PC (windows, max, linux). Rockbox is the LiteStep of firmware. =)

http://www.rockbox.org/

Models currently supported:

# Archos: Jukebox 5000, 6000, Studio, Recorder, FM Recorder, Recorder V2 and Ondio
# iRiver: H100 and H300 series
# Apple: iPod 4th gen (grayscale and color), 5th gen (Video), Nano and Mini 1st/2nd gen
# iAudio: X5 (including X5V and X5L)