Oh - tried to use my Shuffle in Linux and had "issues" - the Shuffle needs whatever program that loads it to write a playlist to it so it knows where all the songs are. If it doesn't get one, the Shuffle "sees" one folder of music - you will hear about 10 songs and then they repeat, and they are usually alphabetical (all "A" bands and artists). Amarok, whatever. I never got it to work in Linux. Most of the iPod dealios were geared towards the larger iPods - where you drag over your whole music library and maybe a few playlists - the Shuffle is a bit more "work it on the computer" and listen later.
I also tried using Winamp in Windows before - they supposedly have iPod support from version 5.something on, but theirs is kind of a pain - there is a plugin called ml_pod which worked much better, allowed for playlists and all. You just have to remember to "EJECT" so the thing will write the aforementioned playlist to the iPod. A pain with this is that any USB memory device you plug in you get a popup asking if you want to manage you music with that device. ITS A THUMBDRIVE - NOT A MUSIC PLAYER.
After you got used to the quirks you could work it well, although podcasts were weird. I had to use a Podcatcher as the built in thing was a HUGE UNRELIABLE PAIN IN THE A$$.
