You may have some success with gtkpod. But, as Chris said, you are better
off with something besides an iPod. I personally use the Sansa Clip Zip
running the Rockbox firmware and it works perfectly. It also supports more
audio formats than the iPods do so ogg vorbis and FLAC play flawlessly.
Think Penguin also sells some reasonably priced players that will work.
https://www.thinkpenguin.com/gnu-linux/penguin-portable-ogg-audio-player-gnu-linux
https://www.thinkpenguin.com/gnu-linux/portable-ogg-audio-player-gnu-linux-v2
http://www.gtkpod.org/wiki/Home
http://www.rockbox.org