And this comes from someone who spent a good amount of his teenage years toying with linux, arch, slackware, lfs, whatever. It was good fun but nowadays I think it was mostly useless and I'd rather had finished dev projects or whatever.

Linux stuff, no problem.

Really depends on what you’re used to, I suppose.

Fast forward a few years a couple of friends around my age introduced me to Linux; it was Ubuntu back when it was hipster and trendy and friendly. I started by dual booting (probably WUBI) and then switched completely.

This is just purely anecdotal, but my conclusion is that it just didn't work when a parent forces a child to do anything. Better to influence the social circle of the child so that the child can be convinced to learn use Linux from friends.

Kids did fine with Amiga or Atari ST back in the days. Linux isn't a problem at all, they'll get used to it. And Valve/Steam proton platform allows them to run plenty of games.

A tiny number of very interested kids did fine, most just ignored computers.

This is false. It didn't take a genius to load a program just by putting a floppy disk into a floppy disk reader. It's even easier with linux. There is nothing difficult with Linux for a kid, nothing that is more complicated than windows.

Setting it up for him means passing up on an opportunity for him to learn by doing it himself. Automatic upgrades means passing up on another such opportunity.

Not a good way to start.