Long time player, first time poster!

Local 2/5 NLHE game, eight-handed. Players at this room are generally capable, some very much so. I assume that players at this room know what they're doing until they demonstrate otherwise. Villain sat down about a round ago, so no specific information about him.

Stack Sizes:

SB (Hero): 650 [87]
UTG: 370
UTG+2: 500
CO: 505

Pre-Flop:

UTG calls 5
UTG+2 raises to 20
CO calls 20
SB (Hero) calls 20 with [87]
BB folds
UTG calls 20

Pot: 85

Flop: [T 7 8]

I flop bottom two, and am happy to check with three players behind and reevaluate, likely planning for a C/R squeeze if conditions are favorable.

SB checks
UTG checks
UTG+2 bets 60
CO raises to 145

Action on SB with 290 in the pot.

DISCUSSION: Do you fold, call, or raise?

I figure the c-bet range is pretty wide for UTG+2, but CO has a pretty well-defined range here.

Value that we're behind (12 combos): J9s (4), TT (6), 88 (1), 77 (1);
Value that we beat (about 16): QQ (maybe 8 combos), JJ (maybe 8 combos); CO three-bets some of these preflop
Semi-bluffs (29): AQ-A2 (11), QJ, 65, 99 (16)

CO has about 240 behind, so half the pot if we call/raise (which, at this point, will probably put him all-in). What I'm interested to hear you discuss: what are the merits of raising here? Do we get more value from hands that we beat? Do we entice UTG or UTG+2 to call with the nut club draw by shoving? Do we err in giving CO another card without a raise? Will the semi-bluffs continue if they brick the turn, or do they not have enough fold equity at that point?

In the moment, I decide that calling has more merit, with the plan of begrudgingly C/C most turns and rivers. There are enough combos of value that we're ahead of that we might get the rest of it on the turn, like the QQ, JJ, or especially the 99. By calling, we ourselves represent basically Ax, some combo draws, or the two pair-type hands like what we have. The whole situation kinda sucks; bottom two OOP is never easy, and facing a three-bet like we are, we are behind some generous minority of the time. Did I make a mistake? How do you guys handle murky situations like this?

SB calls 145
UTG folds
UTG+2 folds

Pot: 435

Turn: [3]

SB checks
CO goes all-in for 240
SB calls 240

Is there any merit to betting out here? I figure since I'm just barely too strong to fold here, and I'm calling most of the time, by checking I give my opponent the chance to barrel with his semi-bluffs and weak value. I'll give the draws their card rather than risk betting into a better hand. Do you agree with this line of thinking? Do you think that CO will barrel with his weak value, even with little fold equity, or should I have bet here?

The river bricks, and CO shows QQ. I breathe a sigh of relief, and scoop.

It is very close, but I think the better and far easier play to make based on the stack sizes is to reraise the flop. There is not much future fold equity here if you call and I don't know if I could fold to a club turn here enough to justify the play anyway. The presence of the UTG + 2 player is somewhat concerning but does not change my play here.

By the turn I would simply lead out and force the draws to get it in.

Note: I made this post before looking at the results

I disagree with your assessment of UTG's hand range. First off, he raised PF and bet into 3 players on a very draw heavy board. His range is narrowed to overpairs , flush draws with 2 overs, or QJcc. CO should know this and given that he flatted pf, he's unlikely to raise an overpairs or weak flush draws (Axcc w/out a pair or 2nd over). His range also includes a lot of hands you are behind with minimal redraw ability (TT, 88, 77, along with QJcc, T8s, and J9). In this spot I would likely just muck the flop and move on to a better spot

Fold or 3bet preflop, I lean towards folding. If you were in position on the button flatting is fine, from the SB I don't think it will get profitable OOP without reads that you are playing vs particularly weak players.
As played Flop is a fold or get in, dont think calling with half pot behind has any merit, you are committed anyway if there is more action on the flop and you're just giving yourself room for mistakes on ugly turns.
As played definitiely donk-shove turn for the rest, you don't want him checking back turn and playing river IP.

I don't mind calling the $20 preflop from SB with a few already in hand. Its an easy hand to release but can realize significant profit. There are certainly merits to just flatting the flop but I think your best move is to re-raise. Based on stacks, its getting in on the turn every single time plus you also don't know how +2 is going to react if you just flat. If you flat, +2 jams and CO calls, you're stuck even worse. x/r>x/c on the flop in that situation imo.

If you want to play the hand, you should reraise the flop, of course, since you have just half a pot left...