1/3, Sunday afternoon, 3 players
Very loose-passive table

There are 2 limpers in early position.
Hero ($470) raises to $16 with Ah Kh.
Five opponents call, including both blinds and the limpers.

Flop ($96): As 3d 3c

Checked to Hero, who bets $50. Only the Villain in the button calls.
Villain is a recreational player who has perhaps folded 2 hands preflop in previous 5 hours. He claims to have won $1000 on roulette before he started. He is also drunk and tired (yawning).
He has a $800 stack, having been lucky with a couple of monsters in the previous half-hour, but is probably down over two buyins this session.

Turn ($196): Kd

Hero bets $100 (has $304 behind).
Villain shoves

Pot is $700

What do you do?

Disgusting spot. There's only one combo each of Ah3h and 3h3s remaining. Can he show up with BS like 4h3h or 5s3s here, or even 9s3s? I'm thinking probably yes.

Maybe we should have checked the turn for pot control if we weren't committed to playing for stacks? A shove (if we checked) would've been easier to get away from, having put in ~25% of our stack. Our hand was ahead of everything except a 4 on the flop, and the turn essentially changes nothing (notwithstanding AA /KK, but does he flat call pre with those?).

The only "reasonable" bluffs on the turn would be with QdJd, QdTd, JdTd, but I don't know if we would really peel the flop with them. In addition, would a fish peel the flop that wide, only to run a huge semi-bluff on the turn?

Has V been playing aggressively or has he been passive? The more passive he's been over the last 5 hours, the more I'm advocating a fold.

Two pair is no good here. Easy fold.

Villain has been very passive indeed. This is the one and only time I've seen him do something remotely like this in five hours. Mind you, I'd been card dead and had played about one hand in the previous hour, it is doubtful whether he would have latched onto that. Villain's in his early 40s and white by the way, and of low social class.

When a passive fish gets aggressive and raises, we GTFO with anything not nutted.

I'm not sure what the point of raising this small is preflop at this obviously loose table. I'd either (a) overlimp and evaluate (possibly to limp/reraise if I feel the raiser is getting out-of-line) or (b) raise a lot more to thin the field. We took the worst route (imo) and built a bloated multiway pot where TP hands (our most likely hand) play horrendous.

Any bluffers in the mix? If so, I might just passively check this dry flop and setup a bluff catcher. Otherwise, I'd bet small to like $30.

Villain being the first to call the flop bet with a zillion people to act after him is concerning as he could easily have a 3. Is he just a loose luckbox that calls anything preflop attempting to hit and get paid off? Or does he make crazy moves postflop? Is he really going crazy here with AQ? Really need more reads on how he plays postflop (especially weak TP) to make a decision here.

Bottom line regardless comes back to preflop for me. We setup a situation where stacks could be played for trivially postflop multiway when we were most likely to only flop TP having given our opponents like insane 35+ IO to do so. Good luck with that, imo.

GcluelessNLnoobG

Can you elaborate on your goals with this turn bet? Do you think we're getting three streets of value from Ax? If villain flats our turn bet, pot will be $396 and you'll have about $300 stack. What is your line on a non-A, non-K river?