1/2NL 8-handed. Table is playing fairly loose, straddles happening about half the time per orbit.

My stack is $325. All relevant villains in the hand cover me and are loose/wide pre except for short-stacked CO ($46) who seemed a bit tighter. Bigger stacked villains in the hand will flat 3-bets fairly wide.

Preflop: BTN straddles, SB folds, Hero in BB raises to $15. (Standard 1st-in open was 15-20). UTG+1, LJ, HJ call, CO goes all-in for $46.

4-bet to try to iso vs. short-stack with $45 of dead money? If so, suggested size?

Flat and evaluate a flop…or min-4bet to try and build a side pot? If so, suggested size?

I’ll wait for replies before getting to the flop…

I would just shove. Flatting feels like the worst option.

Building the side pot is interesting but I'm not a huge fan of that from out of position. If you just flat then the remaining players will tend to play straightforward with the main pot protected by the all-in player. And you can build the pot if you hit something.

Shoving doesn't seem terrible, as I think AA/KK would've 3b if they were trying to trap you. You have a flip against Jacks or Tens.
If they are able to make a big call with QQ, AK, AQ then you are looking at ~30% equity so I'm not sure if the reward $45 dead money is worth the risk, but you do block all of those hands

I can go either way -- $150 or shove.

Very easy 4-bet.

With all the dead money in the pot, and us being OOP, I think I like a raise.

Min-click? I dunno. You make it something small, like $90, or a literal min-click of $76, one or more of these guys might decide you're FOS and get involved with some trashy AX or even 5B you with 99. You're going to end up in an awkward SPR spot post-flop, and pretty close to pot-committed.

I think I'd just jam for max fold equity. You're in the BB, second to act. Your initial raise and 4B jam should look REALLY strong.

Id shove. Id also raise larger like $20-25 pre with the straddle.

Ok sorry for the delay getting back to this…

So because I’m sometimes prone to making sucky decisions (have been running bad, getting coolered, and had just gotten close to unstuck for the session prior to this hand), I just flatted the short-stack’s shove.

It’s pretty clear now that shoving pre is likely the best play.

So, everyone calls, it’s 5 to the flop ($230), and it comes:

Tc8c4d

Is this now just an open-shove with $280 left? I’ll have trouble bet/folding to any raise of a 1/3-1/2 pot bet

This is the #1 thing in poker that I cant stand and sometimes makes me tilt tap the glass like a dumb idiot.

Please for the love of god, DO NOT bluff or semi bluff into a protected pot. It just punishes the deeper stacks for being deep (including the person betting) . You have literal zero FE against the shorty, so what, youre gonna jam $280 in there to slightly improve your king high’s equity vs the shorty? Makes absolutely zero sense. Most of the time you fold out the other guy, which sucks for him, and occasionally you stack yourself, which sucks for you. Only winner is the stupid short stack.

Against 3 other opponents you do not rate to have the best hand right now but your FD+overs represent enough equity to defend against a shove, if that should occur
As Tomark implied, you still have to beat the all-in short stack so a shove as a bluff to win the empty side pot makes no sense.
You could check with the intention of raising all-in.

How tight is the short stack? Does he have us crushed?

We have no IO's vs him oc so we're laying $325 (165 bb's) hoping to win 45 vs a bunch of "loose/wide pre" players?

I don't really like calling (it would suck **** if one of the players decided to back jam on us) and I don't really like jamming either but that's just me. If the short guy has us smoked and if we fold everyone out we only break even anyway unless we out flop him. Weird spot.