The problem isn't the initial installation any more. For Ubuntu and Linux Mint the install process is fairly smooth and the UI is nice during install, and as a daily driver.
The problem now is maintenance, and when things fail...
Yes, I know there's automatic updates, but I ran into an issue with /boot not being large enough to hold kernel images, because after many of those automatic updates, it ran out of space in /boot.
I'm not "technical" enough to know whether I can resize /boot, or if it is feasible - especially with an already partitioned disk. Windows users switching over won't know where to start.
I did find some script that someone wrote to delete old compiled kernels and sources, and keep the last 5 around or something, and now I have to run this periodically, because also, I'm not "technical" enough to know how to configure cron or the permissions necessary to run the script via cron.
I probably could figure it out with 2-4hrs of google and research to get it right for my system, and where I have placed the script based on one of the 20 examples I see on the web, and then cross my fingers to hope it works, but I don't really want to do that at all.
When things fail, sure, maybe they can query AI, but that's probably more dangerous than letting Kevin Mitnick into your home.