My brother in law asked about wrangling 1 PC with a white Ipod (his), a mini (son #1), and a Nano (son #2). I’ve got the same problem, with my wife’s Mini and my Ipod (you are welcome Steve Jobs). There doesn’t seem to be an easy answer, but there are a couple tips.
* Turn "auto-sync" off – Within the iTunes and Ipod settings, you can over-ride the default auto-sync option, so that you have to manually sync your Ipod with your library. This sort of assumes you have one library and the multiple Ipods. But, if you’re not adding tunes a lot, this could work fine.
* On Windows XP, log in as different users – This makes sense, and I wish I would have thought of it. On XP, you can set up a number of different accounts on one PC, so each account can store their own settings, have their own profile, and recognize their own software installs. In this case, he’d have to have iTunes "installed" for each of the accounts, I think. But, that would enable him to a) keep auto-synch on, and b) have different libraries and accounts for each user.
Update (11/15/06): I’ve set up the XP computer to have 3 logins now. 1 for me, 1 for Andrea and 1 for both my kids. I’ve installed the Itunes software for both my account and Andreas. Then, I copied a bunch of songs from my library of iTunes songs to a separate directory for Andrea. And, finally, she’s got her own ITunes account. It’s working like a charm.
Important: Make sure each iTunes user closes iTunes and completely logs off the account before trying to synch the iPod. if you don’t, XP and iTunes thinks that iTunes is being used by another user (because, uh, it is) and can’t figure out which library to synch to. For instance, if I want to synch my iPod, i need to make sure Andrea has a) closed iTunes and b) has logged off. then, I can log into my account and synch it up. Works pretty well when you do it right.
Also, I don’t think i needed to physically copy the tunes from my library to hers. I could have individually loaded the songs and folders into her library, thereby saving some space on my harddrive, but with 80 gigs, i’m drunk with bits and bytes, so what’s another couple gigs, right?
My iPod’s been filling up faster and faster since podcasting hit, and I suspect it to only increase with the introduction of video, with only 60gb on the high-end, soon we’ll have multiple iPods with an iTunes that only understands one.