Villain 1: Very Bad LAG (50/20) in LJ -- probably opens 35% or more of hands from MP, calls 3bets way too wide, and cbets way too often in multiway scenarios (hand history: he opens $20 and gets 3 callers. Flop: 28Qr and he cbets AJo for half pot).
Stack= $2k.

Villain 2: Bad Loose/Passive Player in HJ. Is limp/calling or overcalling his entire range, and playing extremely passive post. He doesn't have a 3bet range.
Stack = $250

LAG in BB. Cognizant of V1's looseness and is putting on a lot of 3bet squeezes to V1's opens.
Stack = $600.

Hero: Stack = $2k.

OTTH:
V1 opens $20 (standard open) in LJ, V2 calls in HJ, CO calls (stack = $600), Hero calls on BTN with TT, blinds fold.

(4 ways, pot = $80)
Flop: 853
V1 bets $50, V2 calls, CO calls, Hero raises to $250, V1 folds, V2 calls all-in, CO folds.

Thoughts on pre: I would normally 3bet squeeze this hand 100%, but, I thought it plays OK as a flat considering the fact that BB is a LAG who may squeeze and V1 calls way too wide. I don't know whether I'm giving up too much value against V1 by letting the hand go multiway a lot of the time, while hoping to induce a squeeze from the BB (and likely call from V1) that may only occur 15-20% of the time. Maybe my play is FPS.

3betting this all day. Not sure why we want BB to squeeze. It's probably going to go multiway to the flop and we're gonna have to shut it down all the times we don't flop a set. 3bet. Taking this down pre is an enormous win and getting it heads up vs the bad lag is also awesome. Going to flop multi-way is the nut low. In general, all the hands that could go either way as a flat or 3b when we're on BTN become much better to 3bet when there are overcallers.

Considering v2 is very passive post flop, what range do you put him on? Is he the type of player who would stack off with A8 in this spot?

Sorry, I should have clarified that I was planning to reisolate if the LAG in BB puts on the squeeze and V1 calls (as he would do with the vast majority of his opening range). So, if BB Lag (stack $600) makes it $150 and V1 calls, I would reraise to $600.

I acknowledge this might be FPS.

I was thinking about this hand because of a training video I just watched from Phil Galfond (the video was circa 2018) where he did hand review for 100NL Zoom 6max online, and he said that squeezes used to be incredibly profitable years back, but players started combatting the frequent squeezes by flatting opens with strong hands. He recommended flatting opens UTG1 (HJ) versus UTG (LJ) with AA, for instance, to help combat against aggressive players behind.

V2 is very loose preflop so he can have any 8x, 67o, etc. He is also very passive pre and post so his range is always uncapped, yet very wide. Yes, I think he would stack off with A8. He only had a bit of money behind after all, and I might have a FD in his eyes.

I guess re raising with TT assuming he would pay you with A8 is very borderline.

Overall, I don’t hate your play but it almost feels too close to “only better calls you” territory and makes villains decision easier.

AP, seems fine, though I'd 3B this configuration and field almost always. Dead $.

As far as 4B a BB squeeze, you're flipping at best for 200 bbs.

I play very little deepstack and am almost never at a table that features multiple stacks above $2K (I'm assuming this is not a small limited BI game), so my two cents are likely already useless but..

I'm mostly defaulting to a 3bet preflop here with all this huge dead money, especially in smaller stack games, but I also don't mind our plan either. I'm actually a fairly big fan of playing very passively at loose aggro tables and waiting for others to get in lol big chunks of their stack before I bring down the hammer with huge hands preflop.

I think the key is that if our plan falls flat (which it did in this case, ok, no biggee) that we don't go all ape-**** postflop with one pear in an eleventeen way pot (especially with V2 still in the mix who can easily be sitting there with AA or whatever). I mean, we're in a bit of a bind on the flop but I think I would lean to a flat and evaluate the turn card and action in position and make our best decision then (especially since I would expect the hand to play out fairly honestly from here on out since it is going to be so multiway on the turn, although admittedly there are a lotta sucky cards).

GcluelessdeepstacknoobG