Strong draw

After villain calls your flop raise and after a total blank card comes on turn, why do you continue betting?

Two reasons. Firstly, I increase the pot size so I have a better chance of taking his stack if I hit my flush. Secondly, he is folding some PPs and weak Js here.

1. You have 9 outs ( not all of them clear, maybe) and you do not have to pump the pot as you will not hit so often to be profitable, and you will have to fold vs a raise.
2. No pair will fold here on that blank turn.

3. You have a FD on a paired board....

I definitely take the point about the paired board (and I'm afraid to say that this isn't the first time you've had cause to make this point to me). And obviously if I'm not getting folds here, "pumping the pot" is -EV. But I don't agree that pairs won't fold. Of course this is mirror-thinking, but if I was in Villain's seat I would fold {KJ-QJ, JT(s), 99-77}. The reason is I would have called those hands as a bluff-catch after the flop raise, but I would guess that Villain (well Hero actually, but you know what I mean) is unlikely to bet again with a hand worse than TPTK. Villain does not appear confident that he has the best hand or he would protect against the flush-draw by either 3-betting the flop or betting the turn (unless of course he has quads or a FH, but that's unlikely).

Which brings me to the question I initially posed, namely is bluffing the river profitable here? However, consistently with what I just said, it seems to me that Villain should already have folded his weak hands, which means that quads/FH now makes up too much of his range to bluff profitably (and he probably does check the river with these hands given I've already bet two streets).

When we raise the flop with a nut flushdraw, we usually want to continue with aggression on the turn/river, no matter if we hit or not. However, I'm not sure that raising a FD on a paired board is the best move. I would just call (probably two streets) and probably try to bluff him if he decided to check at any point.

No need to raise OTF, turn bet is very bad, first off all x is best option IMO, but if you decide to barrel then make it normal sizing like 2/3 of the pot.

Why is 2/3 of the pot normal sizing OTT here? I need to do some work on my bet sizing, but I am routinely betting 1/2 pot OTT.

You can bet 1/2 on a dry flop and bigger on a drawy board.

You should not bet on turn here, though...

When the fish donks on the paired board it means usually made good hand or draw. Since you block most of the FD combos I would put him rather on a made hand which he will almost never fold. Just call flop and check back turn is better imo.

Thanks, that's a really good point.

Were you also trying to represent trips or (that is would trips also be in your raising range here or in your calling range)?

Interesting that villain donked this board with AJo. If you have super-reliable stats you could look at villain folds to river Cbet frequency but in this case villain will look you up frequently I think especially when the flushdraw misses. Also good point on the drawy board bet bigger, on dry boards bet smaller. Raise on flop is ok, you could get a lot of folds but then I would take the check by villain on this turn as an opportunity to see river for free instead of betting again. If you bet turn here even though that card doesnt change too much you would actually also have to bet river to create a plausible line over multiple streets.

Maybe your turn bet was too small to generate enough fold equity. I don't know if the opponent thinks like this but he might not fold a TPTK so easily since it's a steal situation. At least I think it makes his top pair feel stronger since your CO and BTN ranges are probably pretty wide.

However his stats seem like fishy-ish (extremely high VPIP/PFR gap and he didn't buy in for full stack, also a very passive player) so I'm not sure he'd fold a top pair here ever. Probably not the best target for a double or triple barrel bluff? However these kinds of opponents might call the flop and turn but fold most rivers if given enough pressure but I'm not sure if it's necessary trying to run these bluffs too often at the micros.

Also what VaskataBuci said is true and here the bet size tells quite a lot - 2/3 or 4/5 and such is (in my experience) usually a made hand of some kind, mostly pretty strong like he has here. Smaller donk could be a draw, second pair and stuff or just pure air. Depends a lot on the opponent though but this is my experience

Mirror thinking when you're facing a fish is not a good thing at all. Most of the times they don't think and you are going into a deeper thinking when is not necessary. Try to keep things simple against them (fish) and make your life easier... I like what VaskataBuci says, he makes a good point.