Linux

My wife is basically tech illiterate and has 0 desire to ever use something that doesn’t just work out of the box. We’ve moved some of her software to foss (darktable over Lightroom due to their stupid subscription only model) but she’s really only comfortable on a MacBook and even then only after I’ve set the whole thing up and maintain software/os updates.

macOS also sucks for smb file shares so I have a FreeBSD jail that just does xrdp and ssh X-11 forwarding (better color matching for photos this way) and she runs a script disguised as a desktop shortcut to run her apps. The script launches an ssh session and pops up a simple program I wrote that just lists available apps like darkroom. Gives her native file speeds and 0 need to understand anything related to the OS. My rambling point here is unless you set it up so the SO doesn’t need to learn it’s likely to fail and in return you’ll be responsible for all of the maintenance. Unless you’re ok with that it’s probably not a good idea

In my experience, not pushing it makes them want to try it themselves at some point. I guess you need to take care of their computer frequently enough, and are probably annoyed by Windows shitting its pants every time again. Don't make any drama out of it, just point out how ridiculous it is that Microsoft cannot manage to build something that allows running two simple programs without breaking or nagging the user so often. They know that you use something else with which you're happy with, and at some point they will become curious and ask wheter they can have it too. At that point do not promise much, say that it works a lot better but is also a lot different and sometimes a bit quirky. Do not rush it now, let them simmer in their curiousity. At a fitting occasion tell them very briefly about foss and how it is not a closed thing pushed by a corporation onto individuals to funnel data. When they ask if they can try it, tell them they can but it takes a bit of getting used to. Buy a new SSD, and safely store the previous storage in a anti static bag, exclaiming that everything is on there and cannot get lost due to linux. Set everything up with a dead easy DE, give clear tour of how stuff works. With this tactic, they want to get it to work by themselves, and are prepared to learn that some things work differently. It becomes an adventure that is totally revertable if it doesn't work out. In contrast to when you want to force the change and they use everything as a reason to be unhappy about it.