Because all the A5HH Jxhh and 89 J9 ++ can possibly get a free card against us. I hate giving flush draws free cards. Esp on the turn where we can really give him bad odds by just betting half pot.

Im not giving an answer that is correct or that I think op wants to hear. This is how (I) would play the hand

You targettig a small part of his range tho and saying its horrible is horrible too.

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Sorry about forgetting to add the flop betting into the pot.
Yes, the pot should be just about $100 on the turn.

Re my thoughts on the turn: All the people who think that x/raising the turn is bad.
Isn't this one of the best possible turn cards for someone to barrel on?

9T picks up a pair with it's open ended, 67 gets there. 98 turns 2p. There are a lot of other hands that pick up equity against my range esp if I'm just stupid and floating with some overs or something weird. All of those pick up lots of equity against a hand like AJ/KJ and are doing better against an OP now also. I fully expected to get a second barrel out of the flop bettor.

And in addition to all of these hands picking up equity against my perceived range, there are a lot of hands that picked up enough equity that they can stand a check raise when they will be IP on the river. I admit I should have made it a touch bigger, but I didn't have the pot size right in my head at the time (I was thinking the pot was around $90 or so). I forgot to add in the turn bets into my calculation mentally. Likely would have made it $135-$140 or so, and it makes a river shove even easier.

River:
Obviously yeah, I forgot to edit my title. I checked the river and he shoved all in. He had me covered so it was for my effective stack of $265 but I'm not sure that he knew how much I had. My chips were not in even stacks of $100 or so. I didn't even know exactly how much I had until I counted.

Still struggling with trying to give V a good range on the river though. And that's where I'm struggling, why I don't know what is the right thing to do here.

IMO, betting for value >>>>>>>>>>> allowing unknowns with little/no history to bluff.

I feel like after V1 gets called in 2 spots hes gonna be more likley to check back because usally a check raise is what happens after 2 players C/C. Obv you got a 2nd barrell but its just to scary for me when it goes chexk check.

Turn check-raise is really standard.

I'm betting flop with overcard + gutter + BDFD and K or A cards we can barrel on if called. Probably barreling most spades as well.

River I think the best play is a bet/fold of $125. Our range looks super strong on this river and would never expect V to come over the top with worse.

Let me clean up the pot sizes here, because the river is much simpler then I initially thought.

So with $252 behind, the final pot after V2's shove should be $860, requiring just 29% equity to call.

With a SPR of 0.7, there is no way we can reasonably b/f the river for any amount, as played.