I totally understand where you’re coming from, and I’m pessimistic that any flavor of Linux will be an acceptable experience for the person you’re describing. Something like Silverblue may be least obstrusive, but compatibility will still be a prominent problem.

Alternatively, you could show them surface level cool stuff that’s easier to do with Linux. Like blocking all ads, running your own Minecraft server, downloading YouTube videos, building your own PC with cheap parts (and maybe even pirating movies and TV shows, depending on your own practices and relationship to that person). There’s a lot to love about Linux even if you don’t care about privacy and open software as abstract values.

The way I usually start teaching using the console to my (very much non-tech) students is set up a safe container and then let them type whatever, invariably generating a lot of error messages. Then I challenge them to generate different error messages, “gotta catch em all” style. Then we talk about the error messages and what they might mean. After this exercise they usually get the basic idea of command – response, what to look out for and how to compose valid commands.

This sounds like a good idea, but I think the problem here is that a lot of popular software runs great on Linux but is very clunky and ugly on other systems (looking at you, LibreOffice). So keep that in mind if you try out FOSS on Windows as a sneak peek.

ffsend targets Send which is an actively maintained community fork of Firefox Send.

It’s not centralized, you can host your own or choose from the public send instances.

Helpful answer: vlc, libreoffice, gimp, inkscape, zathura, obs-studio

Real answer: gnome, run-or-raise, foot, fish, tmux, fzf, silver-searcher, neovim, neomutt, vifm