Assuming your 200bb deep,

Checking the flop is an option, The board is more favorable to him, although removing his pre flop nuts hands i assume we still have a equity advantage on the flop. Our hand doesnt improve a lot, its a 2 street hand max, 90% of the time.

Against what i assume is a the standard station reg then bet flop he'll have allsort of pairs + backdoor stuff he'll call.  Call turn, fold river. JJ with no fd blockers would be one of the better hands to call and if he's playing perfect id suspect its a call. But the standard 200nl live reg is under bluffing here so just fold.

From the IP point of view its a really interesting spot to raise here, especially the deeper you are as he puts a large % of your range in a shit position if he raises flop then goes to town on a lot of run outs, but be aware of opponent as I.P will be making most of his money from someone paying him off 3streets with an overpair.....

Stack sizes?

He is very good at heads up cash games.

Remember he was losing/break even for years and years he isn't a talented poker player who can jump in and out of games naturally. He dedicated himself to heads up and got good from years of repitition/looking over things and very deep database study on regulars finding their weaknesses.

There's probably 1000+ players better at MTTs than him and probably 5-10 better at hu cash games, that speaks a lot.

He is the very best at poker content in the world right now though.

Hard to really believe that someone who has cashed $5m, majority of it since 2013. and had success in online mtts recently is outside the top 1000 mtt players in the world. Maybe's he outside the top 50 and a spot / Break even in a tough 50k but top 1000s . . . .

I want to improve my reading abilities to the level of someone like Phil Hellmuth.
Other than Mike Caro's book what other information is out there.

thanks in advance