Two villains:

Villain 1 (MP) $60: a young guy I've never seen before, standard weak tight live 1/2 newb. Lost most of his stack last hand when he doubled me up after I flopped a set vs. his KK.

Villain 2 (BTN) $350: a retired dude with a fairly big ego. Has figured out how to beat live 1/2 and is not above reminding everyone at the table of this fact. Prides himself on always showing down the goods, very fit or fold postflop. Last big hand I saw him play he called a big raise (10x) pre with 97, flopped two pairs and got it in vs. an overpair before getting counterfeited. He lost about a $500 pot.

Hero (SB) covers, image is TAGish

UTG limps, UTG+1 limps, MP raises to $15, two players call, BTN calls, hero calls out of SB with T8, BB folds, UTG calls

FLOP ($90): T97
Hero checks, UTG checks, MP throws in his last $45, folds to BTN who calls, Hero?

preflop depends. you're oop without implied odds against the aggressor who already put 25% of his stack in before the flop. multiple callers do make it tempting, but the UTG and UTG+1 limpers make me worried about a backraise. If they're passive and/or making limping in EP an habit, then I'd probably join the party.
flop I check and call. raising would be betting into an empty side pot while oop. I'd call and go from there, expecting the action to go c/c on most turns (obv lean towards betting a J, T or 6). on the river you should sometimes be able to find a thin 50$~ value bet, depends...

Hero shoves.

There is $180 in there. If you call, that puts in $225. I'm sorry, but Villain (on button) has $290 behind. We have enough fold equity here to get a cheap showdown.

Pre I'm not worried about a backraise but I don't have notes/reads to back that up. Hand is somewhat old.

Am I wrong to assume BTN's calling range is weighted toward TP+? Are we ever good here unimproved?

call, and stack button when you hit, take free cards in the protected pot when you don't.

Preflop: easy fold, you don't want to be playing this preflop especially when the initial raiser is an uber shortstack and just put in a quarter of his stack.

On the flop: just call. we have to worry about both utg and villain 2 and we could be behind villain 1. No need to risk stacks in this spot when villain seems straight forward and we're going to win the pot a fair percentage of the time anyway. TP + OESD does not equal monster draw.

pre honestly depends on stack sizes of "two calls". If they are ~200bbs then it's kind of whatever. If they are both 100, it's a fold.

how did btn call? I think we should be raising the flop as when we miss the turn villain can bet and make us fold...i wanna see 0 or 2 cards from this point...