Villain is not check folding turn ever, he's in position so that's impossible.
I don't like floating when OOP. I also think pokerstoving against a villain's hand (instead of his range) is a fruitless exercise.
You're not deep stacked enough to chase a draw, c/c on flop puts in 25% of your stack and you're basically praying villain backs off on the turn after you c/c then check to him again, a line that is begging for a second barrel. Any turn bet from villain commits him.
The problem with jamming turn instead of flop is your odds of catching your flush/overs are cut in two. I like the c/r AI on flop with overs + NFD and a board that's likely to have missed our villain, the only issue is you need to be folding a chunk of villain's range to make it work and the flop bet looks huge for a cbet, skewing his range towards pair or better instead of missed overs.
Basically don't beat yourself up over this one imo, nh