I figured this out around 2005. Get your entire company on Mac, get your entire family on Mac. Your life will have zero support calls, maybe outside of the intial "How do I install an app" which seems to confuse some people.
I told him to just get a Mac- it’s a little more expensive but the user experience is unparalleled, and the Genius Bar offers (do they still?) classes in using your computer if needed.
Never had to help him with buggy software, crashes, etc. It just worked.
Even the first one I owned was straightforward
Honestly, it kinda let me off the hook. "Sorry, I don't know the first thing about Windows[0]. But if you have questions, I'm sure the Best Buy fella will be happy to walk you through it." They never have liked the dumb thing since they got it, but hey, I did my best to lead that horse to water.
[0]I do, but they don't know that, and anyone who tells them's getting throatpunched.