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run Snow Leopard in a VM on a new Mac.
What does this mean exactly?
The thing I liked about my solution was how easy it was for him. I used a trial version of "Crossover" to install the windows version of Appleworks. This meant he just had an Appleworks icon in his launchpad and when clicked, it would just seemlessly boot up, with crossover running in the background.
Would this be the same for your suggestion?
This old dog is not going to be learning any new tricks - so it needs to be as close to how you'd normally use the Mac as possible.
Scrabble-
https://en.m.wikipedia.org/wiki/Virtual_machine
You get him a new(er) mac that works with all the up to date stuff, and then on that you run a virtual machine with snow leopard that has all his old apps and files on.
This thread may or may not be useful https://forums.macrumors.com/threads/snow-leopard-vm-running-in-catalina.2211489/
hugo7
You would also be able to run Snow Leopard in a VM on a new Mac.
Migration Assistant should work fine between the two Macs. I don't think there's any risk of harming the old one.