For me I think Windows 98 VM could be the one. Most of the games I played and am playing can be run on Windows 98. Only a few modern ones have to use Windows 7

For me I think Windows 98 VM could be the one. Most of the games I played and am playing can be run on Windows 98. Only a few modern ones have to use Windows 7/10. So I'm content with that. The only issue is that I don't know how to pick a retro platform for my kid. I never owned a real computer back in the 80s so I know nothing about Apple/Atari/C64/etc. Some people suggested that I should use a modern platform for that purpose (e.g. Pi) and I'm considering that approach. Basically I want my kid to start from something as basic as BASIC and directly go for C or assembly, just like what old timer kids did on Apple/C64. I'd like to introduce some resource restriction and low level programming to him from the beginning (POKE, anyone?).