Haha, I’ve been daily driving slackware since the late 90s. I like to tinker and install a lot of stuff. I seem to break anything with an automated package manager and dependency resolution.
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.
I have att fiber here on the nw side and it’s pretty damn sweet. 1gbps up AND down. I just have to keep dodging bullets, tripping over dead bodies and putting up with a bunch of snowflake libs to have it.