1/2 NL:
Hero (~$750) is early-20s white male who has been at the table a little over an hour and recently won a $650 pot by getting 150BB in on the flop with middle set vs. bottom two vs. FD+gutter.
Villain ($357) is middle-aged white male who seems decent. The only hand we've played together, he raised UTG, I 3bet from MP, a Q84 flop went check/check, and he bet a blank turn and blank river with JJ. I've played with him once before and seen him be a little wacky—he raised UTG with 64 and flopped two pair, but I think he's generally solid. I haven't done anything out of line since I sat down.

Preflop: Villain (UTG+2) limps, one other player limps, hero raises 88 to $10 in HJ, CO calls, BTN calls, blinds fold, villain and limper call.
Flop ($53): 854.
Villain bets $20.
MP folds.
Hero raises to $60 [this should probably be slightly larger].
CO folds.
BTN folds.
Villain raises to $145.
Hero?

Phi Slamma Jamma. Even if he has 76, you're only a 60/40 underdog.

Show him who's boss!

All in......

This is an easy ship. V can have 44, 55, 54, pair + FD/SD combos or even a passively played 99 or TT. Certainly 67 is here but we have enough equity against a flopped straight on this board. Never folding.

Ok, thanks. I guess this is a little more of a no-brainer shove than I anticipated? Any thoughts on how deep we have to be before we consider flatting instead of shoving? In-game, I know I'm not folding, and I hate flatting, so I shoved.

Probably need to be 300bb effective to even remotely consider flatting the flop raise. Even then, I'm never flatting...why flat this flop ever? Deception? No, if we're deeper than 250bb then I'm putting in a 3 bet.

Hm. Conceptually it just seems that at some point, we'll fold out everything worse and it has to be -EV to get a ton of money in as a 40/60 dog with only $30 of dead money in, but I'm not sure at what point that occurs. I could very easily be wrong, though.

No, actually you make a good point...I respect the way you're thinking this through, but you're also fixated on the results. When making EV calculations on this flop, obviously we are an underdog against 67, but that is the only hand. We are a massive favorite against V's entire range on a draw heavy board against a "wacky" opponent. That's a recipe for getting stacks in.

I'm just not sure at what point it's too optimistic to include 44/55/clubs in his range. Is it after he 3bets the flop, or would it be after he 5bets the flop (in the hypothetical deeper scenario)?

If V flops bottom or mid set on this board he's pretty much playing it the same as flopping the nuts, so yes his 3 bet and 5 bet range are similar, the exception being that his 5 bet range will exclude all semi-bluffs and two pair combos, as this V will only be playing for stacks with a weaker set or straight.

How does hero beat straight?
4 5 or 8 ? That's 7 outs.
Rule of 2/4 = 14%/28%
Seems weaker than 60/40

Well, turn and river can also be the same thing. Board can run out 67 for the chop. Also didn't look at suits but could be something there.

Furthermore, the rule of 2/4 is not exact.

I actually think flopped straights vs set is 65/35 in this situation?

The 10 pf is useless, I wouldn't expect any limper to fold for the extra 8, that needs to be 12+.

Ship it.

Stacks would have to be enormous to consider anything other than trying to get it all in. Actually I'm not sure they could possibly be big enough.

I think you could easily make a case for shoving with stacks of 800 or even higher. Smaller sets are pretty much never going to fold. Some people would be unable to fold 54 here. And there are plenty of combo draws that could be in villain's range that have tons of equity.

There are lots of cards on the turn or river that will make the hand difficult to play and/or kill your action. Shoving, even over-shoving, in this spot guarantees that you will be making a decision you know to be +EV, won't have any difficult decisions to make later, can get the money in against smaller sets before a scare card comes, and will give villain a very difficult decision with his big draws which are the hands that could make things most difficult for you.

I think the value of giving your opponent difficult decisions while giving yourself easy ones is hard to over-estimate.

I agree this is a ship, but against a generally solid villain I'm not overly thrilled with this situation. Maybe this is a bad read on my part, but I don't see him having a draw in this spot very often. I think he has 76 often along with 44 55 and maybe 45. I think best case we have about 65% equity.

vs a range of 67 off,67 suited, 44 and 55 you are a 50.61-49.39 favorite, and that's a crazy tight range....I'm raising this wet of a board all day before a card kills the action.

This is an excellent point, it would be much easier to put a younger aggro on a draw. But old solid guys can be surprising especially if they're not just ABC robots, and there are a ton of draws here from his limp-calling range.

I don't think it's likely that he would decide Hero has, and will fold, an overpair. But I'm not going to eliminate that possibility by any means - especially since it's so easy for Hero to have an overpair based on the pre-flop action.

El Diesel, do I want people to fold pre? That's an honest question. I'm usually happy to have people calling my raises when I have mid-pairs, especially when they're calling OOP and with things like 67o.