I don’t think I will convince you. However, I will give you MY reasoning for flatting pre.

1. This opponent will often make mistakes post flop and if we have safe board to continue on, we will.

2. Shoving pre, only accomplishes one thing. And that’s equity denial and we win dead money.

3. When called, we are in bad shape.

4. I don’t necessarily think 99 is a set mining only hand in this configuration when ranges are pretty wide.

I will say, I should have picked a bigger sizing pre. I think we can call pre and play post. If we face a lot of aggression, we can fold and move on.
Also, I don’t think shoving pre is bad. Just wasn’t my preferred option vs this opponent.

I don't think pocket 99 should be treated like a set mine here. But you are saying that ranges are wide here.

If ranges are wide as you just said, why don't we consider 4bet shoving pocket 99?

You mentioned that Villain will often make mistakes postflop. If you think that you are a much better player than him, then that would make some sense for choosing to call preflop to cash in our your postflop skill advantage. But remember that you will be at a positional disadvantage.

As far as "safe flop" for pocket 99, there really aren't many good flops for pocket 99. A large majority of flops will have at least 1 overcard to your unimproved pocket 99.

I agree with most of your points. But I stated the reasons why I, myself, didn’t shove pre. Vs a stronger villain, I would be more inclined to jam preflop.
Wasn’t so much that I think I’m much better. I just felt like he was capable of making a lot of mistakes, considering he was drunk and kinda loose.
I agree with playing hand OOP not being ideal, but when the hell is it ever? Am I right? lol
Either way, as I mentioned, I felt like the better decision Vs this villain pre was just flatting his 3!

If you're targeting Ace high, then why block bet at all? If you bet bigger, >75% pot, then you are making him call down with his bluff catcher instead of the other way around. You are just as likely to get called by Ax with a big bet as with a small bet, so you may as well pump it up and get some value.

I’m going to have to respectfully disagree with this.

If I bet 75% ($375) I believe he is less likely to call off w A highs. I believe that w a small 10-20% block bet, he is more inclined to call w A high, and or potentially bluff raise the small sizing.

Most fish at 1/3-2/5 aren’t bluff catching river bets for 100bbs+.
I feel like a small sizing accomplishes alot more. Larger sizing makes his life a bit easier. Fold mostly everything, call w hands that beat us.

This. And I am quite surprised nobody pointed it out earlier.
A stadard 3bet size from oop is 4x the initial raise, which would be 48 in this case. Given this specific dynamic (straddle and blind min-raise) you can easily make it 55-60.

As played, when V 4bets to 150 our 40 3bet, we are in a tough spot.
I mean, against any standard 4bet range, we are either a small favourite (almost flipping) or a big underdog, plus we are oop.
In game, I probably just fold.
Shoving has some merit, but works best against someone who 4bets/folds JJ, AQ and maybe also something like A5s: not sure this applies to our V.

We are a bit too shallow to call for set mining, imo. Therefore, if we call, we are basically hoping:
1- That V has AK, AQ, MAYBE the occasional AXs
2- That we'll not see any A, K, Q (at least) on the board.

So, as played, the runout is about as good as it gets for us, the line postflop looks fine, but we have to call river.

Yeah, I should have raised larger pre, for sure. I think, in game I didn’t really treat the 12 blind raise as a raise and more like a 4th (double straddle) blind. Either way, I absolutely needed to size up.
Also looked at villains 4! More as a 3!, since his initial blind raise was an any two card, situation. Just a super uncommon spot preflop, as not many times do we face reRaises to blind raises preflop.

FWIW, I am fine with your preflop sizing to $40. You should be treating his blind raise to $12 like a 4th blind.

Generally I agree with this. A blind bet/raise is not the same as a min-raise from someone who looked at his cards.

How we view the blind-raiser's 3B really depends on our reads.

A lot of guys will over-defend or even re-raise as a bluff whenever someone raises over a blind raise. The thinking seems to be a combination of the realization that a blind raise range is any two cards, and the machismo of "not going to push me around".

My point is not whether the blind raise should be consider as a 4th blind, which indeed can be reasonable.
My point is that H is on the SB, so he will play the rest of the hand oop, hence the reason for sizing up pre.

Results:

Easy call. Maniac is always going to try to represent something. He's saying he has an overpair but didn't raise you before? Not buying it.

How big we raise does seem somewhat dependent on how we view the initial blind raise. If we're treating it as a 4th blind, raising to $40 doesn't seem absurdly small, when there's only $22 in the pot when action gets to hero, and V's range is literally ATC.

Could he go bigger? Sure. But if we're $1k effective, and treating V's blind raise as a 4th blind, we're less than 85bb's deep to start the hand. I'm honestly unsure what would be GTO here, but my gut says we'd want enough stack depth behind to effectively maneuver post-flop, indicating a smaller 3B size, even if we're OOP.

If we raise to $50-$60 and get called, we're going to the flop with ~10bb's in the pot. Things could escalate out of control very quickly when our V is a drunk whale. Is 99 really the hand we want to take to war?

Case in point, V 3B's over 3x pre, and the pot is $500 going to the river, with just over 1.5x pot behind. When hero bets $75, just 15% pot, V raises to $500, almost full pot. Like I said in my first post, we can't fold, but we're not fist-pumping calling off with 99 here.

Just because V is a drunk whale doesn't mean he can't have 88, 77, JJ+, or 3x here. We're really only beating his total air-ball bluffs.

Im check calling river all day. 3 bets tend to be higher pair than 99, or AK AQ, and the check back OTT smells like AK AQ and ill let him bluff into me.

As played im calling cuz your blocker bet mightve induced a bluff raise but i dont think its a super exciting call.

If drunk V has been 3 betting a lot preflop, i would be inclined to induce the river raise with the tiny bet, and id be snap calling. But my experience is drunk dudes dont 3 bet a lot.