Probably linux mint. Everything tends to work out of the box and function the way you’d expect. If you’re used to windows then cinnamon will have a familiar feel to it. I like xfce myself, but I move things around to make it feel like windows 95.
I don’t think dubious scrappers taking obviously stolen copper are paying fair market value. You’d have to throw in a vcr or two amd haggle a bit to get enough for a dub.
3rd, but I recommend getting the kde variety (used to be called kubuntu). This will give you the most windows like experience. Regular Ubuntu ships with gnome and has a different feel to it.
I totally get that! Everyone here is suggesting complicated virtualization options. Maybe they know something I don’t. But if it were me, I’d try setting up plain old WINE and seeing if I can install an old version of iTunes from here:
Just curious why the ipod? Is it for retro chic? Are you trying to load songs you purchased or “backups”? I play my backups with vlc on my phone to save data.
Ipods have a proprietary handshake that must happen between the device and the computer trying to manage it. The open source community was able to reverse engineer it on the older models but not the later ones.