I’ve noticed the inverse as in the more I understand something, the less “simple” it looks.
Apparent simplicity usually comes from weak definitions and overconfident summaries, not from the underlying system being easy.
Complexity is often there from the start, we just don’t see it yet.
I suppose we'll just have to agree to disagree. Simplicity comes from strong definitions, and "infinite" complexity comes from weak ones.
If you're always chasing the next technicality then maybe you didn't really know what question you were looking to answer at the onset.
I think it's more of a curve from my point of view.
Beginner: I know nothing and this topic seems impossible to grasp.
Advanced beginner: I get it now. It's pretty simple.
Intermedite: Hmm, this thing is actually very complicated.
Expert: It's not that complicated. I can explain a simple core covering 80% of it. The other 20% is an ocean of complexity.
Wisdom comes from knowing what you don't know.
There's a great analog with this in chess as well.
~1200 - omg chess is so amazing and hard. this is great.
~1500 - i'm really starting to get it! i can beat most people i know easily. i love studying this complex game!
~1800 - this game really isn't that hard. i can beat most people at the club without trying. really I think the only thing separating me from Kasparov is just a lot of opening prep and study
~2300 - omg this game is so friggin hard. 2600s are on an entirely different plane, let alone a Kasparov or a Carlsen.
Magnus Carlsen - "Wow, I really have no understanding of chess." - Said without irony after playing some game and going over it with a computer on stream. A fairly frequent happening.