Played 1/1 game tonight, very passive game. 3 players were huge nits, 2 are calling stations, 1 action player and 1 solid reg.

In this hand my stack is about 350~.
This is around 4 hours into the session, utg opens for 7, 4 players call.
UTG has recently joined the table at this point, no reads on him, but he's definitely not a reg or a solid player.

I'm on the bb with 8Tss. This is a good opportunity to squeeze, but this would've been about my 4th squeeze in a short span of time. the 3rd attempt was answered with numerous calls so I decided to flat this one.

Flop comes 56j with two spades (J of spade).
Pot is 42.

I'm first to act, I check and UTG bets 12. It folds to the BTN (the action player) who raises to 30. UTG has around 90 behind, BTN has 180~ behind.

This player is stuck around 400-500 bbs in the session, this isn't the 1st time I play with him. He has a habit of "flicking the switch" on aggression and attempting a bluff, based on a hunch it seems, so his range here is fairly wide.

I assume folding would be fine here, a bit on the nitty side but fine.
Calling is the worse imo, holding T high OOP in a big pot.
Raising is also fine, a bit on the spewy side I think.

I decided to raise, given that a good sized raise would be around 100-115, I shoved all in for 180~ to apply maximum pressure.

Is this a bad shove or a good semi-bluff? How would you play this hand?

If btn didn't raise I would of x/r flop
AP I fold, doubt btn will r/f anything

Any other comments on this?

I’m generally not a fan of jamming into an uncapped V (UTG) on most flops. The UTG range is probably well ahead of H given his c-bet. BTn has raised this uncapped UTG V and now we jam over the top? We’re just at a severe range disadvantage here to 2 Vs and we have less FE than we need I fear.

Agree that calling is not an option as UTG might well jam if we don’t, although we’d get a better price this way. AP, we set the price of 2-1 for UTG who is probably ahead of us. UTG gets 3-1 if BTn calls! He’s never folding. BTN gets 2-1 if UTG calls and he’s probably ahead of us.

In short, I’d fold because we offer 2 Villains a good price on our jam and we cannot be sure we’re good even if we make our flush. Basically we’d prefer runner runner straight to our flush lol.

Very well explained, thank you! I'll know better next time.