I've done a bit of Googling but as a non-iTunes user I'd like some real user experience if possible.
A customer of mine has ended up with a "ASUS little shitty netbook thing" (his words!) for his daughter, and with the requirement that "all she wants to do on it is surf the internet & manage her itunes on it".
They don't like the noddy interface (presumably Xandros?) and I could replace that for him. But iTunes I know nothing about. I gather that Songbird is a suitable replacement, but I have no idea how similar it is to iTunes and whether it'll allow her to manage her music files.
I don't know much about Songbird, but when I had an iPod I used to use GTKpod to manage the music on it - and I think it's the library from this project which is used by Songbird and other apps to talk to the iPod. However, that's only going to fit the requirement of getting DRM-free songs on/off the iPod. If she wants the full iTunes experience - including being able to buy songs / audiobooks from the iTunes store, then I don't think you've got much option bar trying to get a version of iTunes running with WINE or under a Virtual Machine. There are more open alternatives to the iTunes store, of course, if she can be persuaded to use them.
If she just wants to be able to rip music and stick it on the player though, it should be fairly straightforward.
It has been over a year since I did this sort of thing, though.
Peter.