Getting things working can be complicated with GNU/Linux distros, some more than others.
Ubuntu has some of the best support for peripherals out of the box, and Kubuntu may also be like this (I assume they just swap GNOME for KDE, but I'm not sure on the specifics).
My suggestion would be to decide what distro to go for, and ask all your questions in their forums, where people far more knowledgeable about that distro than on here can answer.
Which iPod? My suggestion would still be to get a dedicated separate hard drive, and do a proper disk image of your current Windows setup to that (and not just copy some files and folders), so that if everything goes wrong you can still get out of it without too much mess.
DriveImageXML will let you do this (for free),
http://www.runtime.org/dixml.htm