I also switched my parents off Windows to Ubuntu for a while (when I used Linux desktop myself and before OS X). It worked pretty well and didn't cause them too

I also switched my parents off Windows to Ubuntu for a while (when I used Linux desktop myself and before OS X). It worked pretty well and didn't cause them too much pain. Subsequently of course I got them to switch to Apple and that's even better, primarily because they don't have to feel that they're using some weird thing their child encouraged them to use. Avoids the Windows nonsense of computer getting slower and slower all the time, and malware. The only thing I've failed to help them with is the baffling Apple stuff surrounding iCloud and storage on multiple devices.