Oh man, I just discovered this guy recently. I'm way into his bendix project. I really hope he gets the thing running and shows us what he can do with it.
Obama tried to do a similar move through an executive order near the end of his second term. My job at the time scrambled to give me a raise just above the proposed threshold. I declined and said I'll take the time and a half. Ibwas routinely working 60+ hour weeks at that time. Trump repealed that order early in his term, and I didn't get that raise. I left that job a few months later.
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.
Tiling wm or cli only, Satan's crackpipe?