> I wonder if the steamrolling incentive is also why so many people eventually “hit a wall” in their math studies. You can only get so far without a solid base for a cumulative knowledge area like math.

There is a known (but mostly ignored) educational method called https://en.wikipedia.org/wiki/Mastery_learning -- you should teach kids until they actually get it, and only then move to the next lesson. This method may be slower at the start, but later gains speed because kids with solid background understand the new concepts faster, and do not need to relearn the old concepts all the time.