There's a chunk of relevant history and some solid guesses that we can make about Villain in this hand, so bear with me for a bit. And really I'm looking to start a discussion about the best profit-maximizing line, both on the flop and planning for later streets.
Villain is mid-20s, grinder-looking player, wearing hoodies and sunglasses. Has been playing with Hero for 6+ hours. Overall seems like a very solid, good thinking/winning player (meaning has no obvious leaks, sizes bets well, understands value-betting/bluff-catching/position/relative hand-strength/etc. all that good stuff). I have every reason to believe that Villain has also been observing me as much as I have him, and he probably sees me as being a similar player type as himself, except that I'm probably a tad looser/more aggressive than him, and that I tend to size my bets a little bigger than him as a general thing.
There's probably 4 hands of relevance to the main hand in question:
1) Within 15 minutes of first sitting down, Hero decided to 3bet-squeeze a $15 open from Villain after 2 weak calls, to $85 w/ K6ss. Got cold-called by the SB and Villain called as well. Flop was As5d6h, I cbet $145 when checked to, the SB called, and we checked it down from there; SB showed AQo and I mucked. Was surprised by the cold-call with AQ, but shrug w/e, made a note and rebought.
2) Exactly 2 hands later, I 3bet an older player's $20 open to $75 w/ AKo, got cold-called again by a different SB player, and the old guy 4bet to $325. Normally this is probably a fold, but the table had talked about wanting this player to stick around cuz he was fishy/spazzy, so I figured that 5bet jamming AKo for ~120bb wasn't the end of the world here based on that (also sizing seemed weird for KK/AA but I wasn't reading a lot into that). Mainly I just figured I looked really fishy/tilty, so w/e let's flip. I jammed, he called w/ JJ, and I flopped a K. Old guy proceeded to tilt off about $1500 afterwards, so that was cool.
3) Back to Villain with this hand, he opened to $15 pre (his standard), got 5 calls, and flop came 874dd. Villain underled for $30, one player raised to $75, Villain reraised to $150, other guy made it $350 total, Villain makes it $700 total, and the other finally folded even though he only had about $400-500 behind (!!). If I had to guess, I would put Villain on the nuts/super-nuts here (76dd). I didn't think they had enough of a dynamic for him to be 5betting here with a nut/combo draw and expect to get a fold, especially cuz the other guy easily has the nuts in his own range and/or would just call it off with a set to draw at his boat, given the price.
4) Ok, this hand is actually between me and the Villain. Villain straddled to $10 on the button, folded to me in the BB, I open to $35 with 88, and pick up one MP caller along with Villain. Flop came Q76r, I decided to cbet $50 into ~$100, knowing that everyone expects me to cbet nearly 100% here, and figuring I was going to get called pretty light or just straight floated by airballs/gutshots. MP folds, and Villain tanks a bit before calling. Turn is a 3, rainbow board. I check, expecting Villain to bet all his floats, and he obliges for $75 into the ~$200 pot, and I call. River is a J, which actually hits some of his floats, but I can't really do anything but c/c, and Villain bet again for $160 into ~$350, I tank for a bit before calling, and he turned over 53ss. Before this hand, I had been bet/folding or bet/giving-up-on-turn a lot w/ my cbets, and I feel like maybe the table thought I was just habitually firing one barrel at every board (really they were just good textures for me to cbet, and my opponents kept hitting pairs or better).
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On to the actual hand:
Hero is MP w/ ~$1800, opens to $20 with 88. Folds to Villain w/ ~$1500 who 3bets to $55 from the SB. I think 4betting is an option, and being this deep and in position, we could probably get away with it just fine, but I chose not to. If someone wants to talk about it, I'm all ears, but I think flatting is obviously a fine option.
Flop: J
8
5
, pot: $110.
Pretty bingo flop for us, wet enough to entice action from a lot of hands. Villain leads for $30 (seems to be his trademark to underlead spots like this, and I fully expected him to reraise me a high % of the time). I make it $130 in-rhythm (thoughts on this sizing?), and Villain takes maybe 5-10s to make it $280 total. Counting our bets so far, pot is now $520, and we have about $1200 left to bet.
Who flats and who reraises?
If we flat, what to we do on 4/6/7/9/T/Q/K/A/heart turns? How often does Villain have a draw vs JJ-AA here? What do you think the min-3bet preflop means (never seen him 3bet for this size before, have seen him 3bet once or twice for normal 3x or 4x sizes after a bet and 1-2 calls, and people just folded; always just assumed he had the goods).
Raising is obviously a very good, +EV play, and I think it's safe to assume that raising by default here can't ever be bad. But is it the best play? If Villain doesn't have many draws because of his preflop, OOP 3bet, then flatting is much, much better right?
There's just so many things going on with this board that I had a hard time figuring out my turn/river plans, based on how the hand might play out if I flat or if I reraise.