Hello, thanks for checking out this hand.

I didn't have a great read on villain. My impression was that he was a competent player (using the chat box which I usually find indicates strength). VPIP / PFR = 22 / 13 but only after 25 hands or so. He seemed capable enough to recognize when a flush comes in.

Obviously I misplayed this hand and would love to get some feedback on it. I think the following were mistakes that I made:
1. check-raising the flop multiway on a connected board
2. leading out on the turn after villain check-called my raise (unlikely that he'll fold better or call with worse)
3. I think that the bluff on the river to represent the flush was reasonable as my betting line was consistent with a FD in my opinion.

Would appreciate comments on the above or on this hand. Thank you!

I don't like it, reeks of fancy play syndrome to me. Couple of points:

I would disagree with this. Competent players generally don't use the chatbox, so I'd be learning towards the assumption that he wasn't competent.

I'm not sure I agree with this. It was the backdoor flush that came in and, for me, villain possibly has more backdoor flushes in his range than we do after the flop check/raise.

I agree with everything monkey said. It is also worth noting that villain posted the BB out of position instead of waiting for his blind, which is another sign of a weak/beginner player.

Flop check-raise is terrible. What are you trying to represent there? You raised preflop so your play on future streets has to reflect that. Don't just make moves, you always have to be thinking about what hand you are representing or trying to represent. Also, it's much smarter to x/r when you have some reasonable chance to improve. All you have on that flop is a pair and backdoor gutshot draw. That ain't worth much.

Your reasoning about representing the flush on the river is way off. There is almost no chance you could have made a flush on the river and any thinking opponent will realize that. Getting back to my first point, what specific cards are you representing with the way you played the hand that give you a flush on the river?

Preflop - Why are you beting J9o here? There are legitimate reasons to do this, but this could very well be a leak in your game if you aren't comfortable playing wide ranges of hands.

The check raise is a clear error, but once you see the CO call here, you should proceed very cautiously. I think this is a good example of an error which cost you little at the time, but lead you down the path of trying to make fancy plays to try and cover for it.

The turn bet is even worse. You might as well have 32o here as no hand you beat is going to call you down here.

Nobody is folding due to fear of a flush on the river here.

I think we're a little results oriented here. The villain caught 2 pair. on the turn. Unlikely he calls river without it (although we'd be bluffing with the best hand here anyway), or A9, regardless of the bluff making sense or not.

However, the line absolutely does not fit a flush draw. If you flopped a set, or straight, why would you risk letting it check through? Same with QQ, KK, and AA which would always bet this wet board since so many turn cards kill your hand.

Also, you have to be dynamic. Preflop, J9o is too lose from MP2. Maybe even too lose from the CO. Ideally, CO and BTN fold, you play vs. the blinds. But when called, playing OOP to players, you have to be much more careful. Change the plan, you flop super marginal, be ready to bail. As played, you can represent nothing because you'd just bet everything. Maybe represent a flush draw by check-calling but everything about your line is so sketchy.

By bombing river how do you possibly have a flush? AK/AQ of hearts that checkraised flop with backdoor hearts? Then the Qh peels turn, meaning you can't have AhQh anymore?

I do think sometimes you can still rep a flopped straight/set and play it like this (you'd still shove river for value even with the backdoor flush getting there with a straight, your sets+2pairs become full houses, obvious shove), which makes more sense than a backdoor flush. But you said you were repping the flush and not a straight unafraid of the backdoor flush. You have to work on your thought process of what hands play in what manner.

Thanks for these comments. They are very helpful to me. Looking back at it, I am really representing almost nothing and my line makes it easy to call my river shove.

Thanks for everyone's insight!