If he called you with a hand that he was supposed to fold, its usually a signal that you targeted wrong player profile with your bluff. That being said, its really tough to commit huge mistakes against in live play having that much equity OTT.

Given that he's lead smaller on the turn than he did on the flop it seems very obvious that villain has a weak showdown hand. I think a shove is fine here, if you want to raise you can't really go any other sizing and we have quite a few outs against the range villain should have.

One thing to think about is whether villain actually finds folds in these spots. It's all well and good knowing what kind of range they have but if they're never folding it then it's a bad shove. Especially as we've been given such a good price to peel.

So basically if villain bet/folds a lot when betting this sizing then the shove is fine, if villain often calls then it's more likely a bad shove.

Yeah good shove. Value of a bluff is always EQ combined with perceived fold EQ. He should fold weak pairs (obv. he plays far from optimal and probably just random feel based). You got worst case 7 outs, but against his range you have 9 flushouts + 6 pair outs quiet often so the shove is good.