Something like Ubuntu these days feels to me like Windows 7, which in my opinion was peak Windows. You can sit down, find your files, install software relatively easily, and the settings are pretty intuitive.
Obviously there are edge cases, but generally speaking, any random machine I've put Ubuntu on just works.
I usually don't have an issue installing Linux on a computer. The issue generally pops up when the recipient wants a piece of software that is only available on windows (which is also true for people migration to Macs). It's one thing to learn a new OS, but having to learn new software generally becomes the sticking point.