This is a pretty specialized problem, but I can't think who else to ask. I'm putting together a laptop for my little sister, who is an 18-year-old Asperger's kid. She currently uses Windows XP, and I'm trying to get her onto Ubuntu. She's used my Ubuntu system with no difficulties, so there's not a problem there.
The issue is iTunes. She has an iPod and uses iTunes to manage her music. Ideally, I'm looking for something that's a fairly direct translation. What I absolutely must have is something that is equally easy to use, into which I can transfer all her iTunes music, and is able to interact with her iPod Nano in all the same ways iTunes will.
Ideally, something with a store would be good. I've used Amazon, but their downloader doesn't play nice with Linux. I haven't used Google Music, but have heard good things. I used MediaMonkey quite a while ago, but could never get it to work reliably with any portable player.
What I don't know is what will play nice with both Ubuntu and the Nano. The most reasonable suggestion I've gotten so far is "use google/amazon for shopping and storage, use winamp for playing and syncing." That seems like it will work, but I don't know if anyone has any better ideas.
I'm willing to do a considerable amount of setup, as long as I can be reasonably certain that I'll never have to touch it again.