If you have tracks in iTunes you can export them as MP3's and move them to pretty much any audio player. If they are iTMS purchases, they will have to be burned to Audio CD first, then ripped into MP3.
Unless I'm missing something, just what I said: Burn the playlist from iTunes MS to an Audio CD. Re-Rip the Audio CD as MP3 format. Move the MP3 files to _____ music player. Play.
You're not gonna be RUNNING iTunes the Mac or WinXP application on any palmtop or portable device nohow.