Switched my Parents to Linux
I don't believe in making GNU/Linux look exactly like Windows. It's a different OS, and any attempt to fool users will be in vain.
I tell family members: "I don't know anything about Windows/macOS." (Because I don't, at this point.) "I can only help you if you use what I use." Usually, they stop asking me for help, and that's great for me. If they say yes, I install Fedora with GNOME and whatever applications they expect to use. After a brief explanation of how GNOME works, people generally get used to it and are satisfied.
I share my laptop with Mom. It runs GNU Guix System with GNOME. She uses it to run Chrome for stuff she can't get on her tablet. She's used to it at this point.
