Anecdotally, I think it depends on age and family more than anything. I grew up with hand-me-down computers, games because we couldn't afford anything new. Started with win98 and games from the mid 90s, but running them in 2002.

I do remember having to look lots of things up and figuring out why some things wouldnt work. Then getting into building our own computers (because it was cheaper) and figuring out how to get halflife mods working...