I played this hand last night in a 1-3. Villain was very active when I sat down, opening for $30 several times in a row and CB-ing hard the few times his raise was called. The only hands shown down were strong, like KK etc. Then he goes in a hole for a while and I realize he was just getting a lot of cards. He makes some weak ass bets with a weak holding. He has folded to a few continuation bets.

My read is that he is not afraid to put money in the middle and that his bet sizing is strongly correlated with his hand strength.

He has about $350, I cover.

V opens for $12 utg, 3 calls, folded to me on the button, I call with 99

Flop: $60 468
Villain bets $30, 2 folds, I raise to $95 As this is not consistent with my read of what he bets when he likes his hand and I want the pot now. My intention was to bet fold. He tanks for a long time. Genuinely looks like he is considering both raising and folding. Is staring at me hard. He calls.

How'd I play the flop?, What is a good plan for various turn cards if checked to. (I am likely folding to a large bet on the turn if villain donks and I do not improve)

Normally I would say your play here is awful. If he's at least moderately competent, he's not cbetting OOP into four players without an overpair, and he's never folding an overpair.

However, the fact that you said he has been opening big with big pairs and he only opened 4x UTG here leads me to believe that a) he is not moderately competent and b) he probably doesn't have QQ+. In this case, I think your raise here is fine under the condition that you think he's opening a fairly wide range here UTG. If he checks turn to you, you should bet here all day unless a heart peels, in which case checking back is fine.

Say a black 2 comes off. Pot is now $150, what's a good bet? About $250 behind.

What about a K?

I don't mean to sound critical but you need to have a plan after the flop once you make that raise.

I'm not saying that the flop raise is bad, but having made that play you've kind of committed yourself to making a big bet on the turn if you want to win the pot. What range do you put him on once he makes the call on the flop? Is he calling with two overcards? (eg AK, AQ, KQ etc).

My general plan was to bet about $90/fold and take a free showdown, but I am posting because I am interested in how the forum would think through a hand like this since it is not so uncommon with a middle pair. I also am happy to be criticized. that's why I am here.

I put him on overs when he made the weak bet on the flop. His call of my raise made me lean towards middle pairs, though I still felt that he'd have bet big with JJ QQ. It felt a bit like a trap or a heart draw when he called.

Turn gets interesting and I have to make a new plan. I spiked the 9 of diamonds and bet the pot.

This is a spot where I see a lot of people make a mistake and bet standard 2/3. The problem with that is that you are NEVER folding the river and the stack sizing makes this spot awkward because you are giving him pretty good implied odds with any bet if he has some sort of draw. Therefore, I would lean towards a bigger bet of around $130.

The fact that you spike a 9 shouldn't really change your plan too much. I'd still bet around $130.