New player here. So not sure if this is done now or not, but maybe could you make worlds with some randomness to them and some historal. You could start small then do bigger ones. For example, a small would be making planes come out more random, you can't very too much as technology advances and does not make since, but instead of a plane always coming out sept of 1960, have it random for five years, so it could come out anytime between 1958-1962. For a bigger example it would be to randomize demand and infrusction for all airports, so there is the same number of each type but no one knows which are big and you have to pay attention.
Not sure how big of a organization this is because it would be lots of programming, but would add flavor for seasoned players and help new players as it levels the playing field about knowledge of everything. Seasoned players having memorized everything.
Just a thought.
main difficulty there : game balance. Randomness is very hard to balance properly.