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He probably will have to switch at some point (especially if he hasn't at least put a VPN or other protections in place when browsing online). As legacy machines are targets that malicous actors want to use for their botnets. As no security updates is a heavenly thing for that lot.
However, it's very unlikely that he'll ever change the situation unless it goes pear shape for him. Not having the motivation, initiative, or desire to learn about changing his OS...Means it's not going to happen easily and it has to be on his own timeline. General computer users don't care for these things, and that's fine. I was like him at some point before I got really interested in Linux, then I got reasonably proficient in doing basic stuff and sometimes complex things on my numerous distros that I tried.