After his check OTF, I don't think there are many hands that can call two streets, a 7 will bet anyway and I my hand needs no protection. I like check raising a lot of turns against delayed c-bets so having one of my strongest hands there makes sense.

I don't like my check since I miss the chance to get one small bet from weak hands. In the moment I probably overestimated the chance to get a bluff on the flush card from someone who declined every opportunity to bluff before.

Against his pot sized 3-bet I am confronted with conflicting information. On one hand I don't think there is a big chance he checked a flopped set (the two hands that beat me) behind twice but on the other hand his bet indicates that he has no fear (or is completely full of it). I think folding is out of the question but can we actually raise his last $2 profitably?