Bluffing three streets against a recreational player

I think the mistake is otf: do not cbet into two players with so little equity, just check back.

As played, ott you got rid of one V and picked up a double gutter, so it makes sense to double barrell.

River is awkward. On the one hand, you have to bluff, but on the other hand, I have no idea what V may fold at this stage.

I don't mind a flop bet, but randomly half pot isn't great. Would be happy to bet 15/20, note that we can have a bunch of draws like this here so we have to be careful.

Yes, you picked up equity on the turn but it's not enough to try bluffing V off much and we don't want to get x/r off our equity ... randomly half pot might be fine, but would be happier with that size if we'd bet less on the flop.
We are allowed to check, even though we picked up some equity.
Going big with this hand from the BTN feels bad.

If we'd bet less on the turn, river would be an easy small bet targetting better draws (spade flushes or KJ).

With the big bet on the turn, I'm less sure. We are kind of saying we had a strong hand charging draws the max. Could maybe argue for a third pot anyway, still targetting better draws. Shoving trying to get folds from Tx, and maybe some weak Qx but that feels like we are praying he folds most of range, would much rather have an A, K or J in hand to try something like this.

i dont cbet this board 3 ways. there are too many ways for people to continue here. even HU checking sometimes is probably best, because anyone who isnt an idiot knows you are wide on the button and usually have nothing that strong on this board.

why cbet so much?

Agree with others who say flop bet is too wide.

When we do bet this turn, I like an overbet. 150 to set up ~pot size shove. And while I wouldn’t have this hand in my turn range, we should have some bluffs that don’t interact with our obvious bluffs (non spades and non broadway, coming from diamond draws, 4X, maybe small underpairs) and these bluffs should strongly consider barreling turn and finishing on the river. If I got to turn with this hand I would overbet it. All of the obvious turn bluffs make poor river bluffs because we also block villains autofolds.

Then on river we default to dropping a bunch of bluffs because our value range narrows, and we probably adjust further by bluffing even less depending how nitty villain is. If we think they fold flush draws and OESDs to the overbet we just don’t bluff river, if we think they call with those hands we finish the bluff with hands like this that unblock those missed draws.

On this specific river I think we’d go with low frequency bluffs, and a half pot size (or smaller if we want to be really exploitative,) bluffs gets folds from worse than QX, we get raised by QX and call with AQ and better

Grunch:

I don't c-bet this. It's blind vs bu, ranges are wide generally speaking. BB range is wider than SB, sure. I still dont think you generate enough folds on the flop vs two ranges to make this long term profitable. Additionally, when you condense the SPR, you need a stronger hand to continue later in the hand. In this instance, we need back door equity just to decide if we can bet again.

The only better turn card would've been 6d or 5d. If we got a 6d, I like a barrel better. I think I take my equity with 6c.

Based on your turn size, the majority of the villain's range will be missed draws and Qx. A ten should have folded turn. KJ/J9 would be ambitious to continue with if you're the villain.

Qx doesn't fold and a missed FDs doesn't need much motivation to fold on the river.

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PRE - seems fine.

FLOP - multi-way with a sticky V in BB, wet board, think I'd either check back or c-bet smaller, like $15, or $20 at most.

TURN - nice to pick up the sneaky double gutter, but no draws complete, and this card wouldn't appear to help our range. V could be trapping, so I think I'd barrel smaller, like half pot.

RIVER - I don't like this card or our specific combo to bluff. V is never folding a Q, and probably not a T, unless we bomb it.

If V is sticky enough to get here with middling pairs, but will fold to a triple barrel, we could probably bet 50% pot to make it look like we have thick value and want to get called.

My thinking is this sort of V likes to hero call vs big bets, but hates to look stupid by calling vs small bets.

The problem is we block some pairs we're trying to fold out (88/77), and it's hard to think he's getting here with 22/33 or 55/66. So really we're trying to fold out 99, and a sliver of worse PP's, along with all his unpaired Ax/Kx combos.

If I have a read that my opponent is "sticky" and "tricky" I'm gonna dial back the bluffs.

I would check the flop 3 way. This board hits your opponents range.

Your turn sizing seems awkward in that it's not small but it's not big enough to set up a comfortable river jam. I think you either have to go far it starting with a turn over bet or bet smaller.

I dont mind the cbet, wouldve probably gone $20, but fine to check and either give up or delayed cbet.

OTT I think a turn bet is great but im betting like $160 to put TPNK, SDs and Tx all into a really tough spot.

River is a terrible card, any Q isnt folding, any T or PP is less scared now that another Q was removed, so all his bluff catchers are calling.

What I like to do on a river like here is to bet super tiny, like $75, to rep a weak made hand looking for thin value, like AA KK here. KJ and J9 will fold without thinking too much about it, and occasionally people will spaz out and fold a bluffcatcher because a bet that small couldnt possibly be a bluff!

I also think betting flop, checking back turn to realize your huge equity, and then betting river if he checks again is a solid line. Betting turn and getting raised is obviously a disaster.

Does the read that V is sticky and tricky affect your approach to the turn?

I get uncomfortable in spots like this facing V's like this, who will show up with all sorts of hands they won't fold before the river. I don't like bloating the pot in the hopes of hitting our hand, knowing V is less likely to fold to a third barrel on a river brick, and will almost never fold if the board pairs.

I do think the bet-check-bet line is reasonably credible here, and like the idea of betting the river small to look like some weak value hand. Just not sure about betting huge on the turn against this type of V.