An important idea about reading is that part of the pleasure (maybe even more than that) is one's choice of "this book, now". I had read many hundreds of books a year by the time I got to high school, but I balked at reading books chosen for me in a class. I suggested instead that the classes deal with themes and that there should be several thousand good books in the library that students could choose for themselves. This would make the discussions of the themes quite interesting, etc. But no go, so I wound up -- for their chosen books only -- reading "Classic Comics" like most of the rest of the students (I did get around to reading the "chosen books" later in life.)
The approach of lots of books and themes was used by Mortimer Adler in putting together "The Great Books of the Western World" (now 60 of them). https://en.wikipedia.org/wiki/Great_Books_of_the_Western_Wor... Besides these books he picked 102 "Great Ideas", wrote an essay on each one, cross indexed the ideas through the "Great Books", and published the essays as the two volume "Syntopicon".
In this sense, the reading list I came up with for Anderson Consulting was too short -- it wasn't a decent library size. And this is true of the "Great Books": it's too short as well.
Another idea is the "Oxbridge" approach: pick "4" important as orthogonal as possible large subjects, and go deep on them until they meet in "the good stuff".
Simplest heuristic: read a lot.
I've been playing Factorio  , which I think would resonate with your love of Rocky's Boots, cellular automata, queuing theory, visual programming, system dynamics and distributed control systems. It's in the spirit of John von Neumann's 29 state cellular automata  and universal constructor. 
 Factorio: https://www.factorio.com/
 HN Factorio discussion: https://news.ycombinator.com/item?id=11266471
 John von Neumann's 29 state cellular automata: https://en.wikipedia.org/wiki/Von_Neumann_cellular_automaton
 JvN Universal Constructor: https://en.wikipedia.org/wiki/Von_Neumann_universal_construc...
I think I'm so out of context wrt video games here and now that I can't come up with a worthwhile reply. I liked Rocky's Boots because of the brilliant combination of the content and the idea behind the game play -- and they were well matched up. I liked the idea of its successor "Robot Odyssey" a lot, but advised the TLC folks to use something like Logo for the robot language rather than the Rocky's circuit diagrams (which were now not well matched up to the needs). As you know I really tried to get the Maxis people to make "Sim City" a rule based system that children could program in so they could both understand the generators and to change them (no luck there).
If I were to look around today, I'd look for something where the underlying content was really "good" for children -- I doubt that cellular automata would be in my top 10 -- and then would also have good to great game play.