I don't think the question as posed is particularly valid. It's not about "classic" vs "newer." It's not even about games. It's about the philosophy of parenting and how it might involve various aspects of our culture (wherever we are, and however we define it). We each need to make our own decisions, as parents, in terms of the types of games that we might want our progeny to sample, and they are going to be derived from who we are as parents and as people. Do we wish to enforce our ideas of what games/movies/sports/music are and should be? Or do we want our children to discover themselves and the things that will excite, stimulate, and invigorate them?
Obviously these are big questions and there are many right answers. For me, as a father, I want my son to engage in games that stimulate his creativity, regardless of era. So far, that's been easy, because that is where he generally wants to be.
In terms of operating systems, I watch where his interests go, and lead him towards things that might further develop those interests. While I might explain to him, or show him, the CLI of linux/unix systems, it will always be in the context of "here is why this is cool and powerful," with a concrete example that was arrived at naturally. It won't be forced. I'm also a musician, and the house is full of instruments, and yet I never force him to play. I want him to arrive at the joy of music naturally, or not at all. Same thing with art ( and all other things). I think that there is a larger question inherent in the question posed, as I said, and it needs to be understood.