The current version of iTunes runs on any of the last 4 OS revisions, covering about 4 years and probably 10 years of hardware at a minimum.
At the time, the hardware was 4-5 years old (iBook G4, 3rd gen nano; you do the math).
One nice thing about Macs is, no, it's really not a "fucking pile of grief.
Oh, it was. The OS/X upgrade wasn't free, for one thing. Apple fucked up and sent the french version, because apparently that's the default language they send to Canadians. Eventually got it, and the install was... well, after a couple attempts it worked. Don't get me wrong, it was still easier than installing Windows, but it wasn't fun.
I assume they've gotten better in the last decade, but I definitely identify with the previous poster about his ProTools experience. When Apple stuff works, it works well and in harmony with everything else. When it doesn't, it's not pretty.
About six months later the hard drive in the iBook croaked. I can assure you that "fucking pile of grief" is exactly the way to describe the process to replace the hard disk in an iBook G4. What kind of psychopath assembles the entire device around the part with the shortest expected lifespan?
Hell, I imagine the same type of behavior is even coming to Linux through systemd.
Most Linux distros have been in a continuously updating state for at least a decade. You do get "major" version bumps periodically which require a bit more clicking, but even those updates are pretty painless... I think the last time I needed manual intervention was 2008-ish. systemd likely won't change anything there, except maybe make the process more brittle for a while until things migrate over.