Trouble spots illustrated by ~600+bb pot

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Trouble spots illustrated by ~600+bb pot

Blinds: $0.25/$0.50 (6 Players) CO: $137.52
BN: $90.89
SB: $49.00
BB: $157.83 (Hero)
UTG: $638.34
MP: $75.12
CO was playing ~90/50 and 3betting very wide as well. They got their stack above $700 at one point, but recently lost a $650 pot to UTG. (No, really, this is PLO50.) My notes on them up through this hand: "seems to overplay EVERYTHING but maybe not bluff a ton; checked bottom two tho; can semibluff somewhat light; checked flopped nut flush; does have some river bluffs". I had also seen them 5bet Ad5dQh6h preflop earlier in the session.

SB is unknown, new to the table.
Preflop ($0.75) Hero is BB with 8 T 7 J
UTG calls $0.50, MP folds, CO raises to $2.25, BN calls $2.25, SB calls $2.00, Hero raises to $11.75, UTG calls $11.25, CO raises to $51.50, BN folds, SB calls $46.75 and is all in, Hero calls $39.75, UTG folds
Nice double-suited rundown, obviously. I 3bet pot because I really wanted to isolate against CO if at all possible, not only because they're such a poor player in particular but I'd prefer to fold out some higher diamonds and spades if I can.

It didn't exactly work like that. When I'm in situations like this (which come up relatively often), I'm not sure if I'm making a big mistake or not. When I get sort of "whipsawed" with a DS rundown, I feel like my equity/playability against the types of hands likely to be jamming preflop is too high to fold. For example, when I calculate the equity of this hand versus two 5%6H ranges in PPT, it's a slight favorite! But I feel spewy in this situations. But I also feel like I can't fold. So I'm finally posting about the problem on RIO!
Flop ($166.00) Q 2 3
Hero
Postflop is a somewhat different problem. (The effective stacks between CO and myself are ~$86 in a ~$166 pot.)

On the flop, I'm not sure what the best line is.

If we shove, we can potentially get a better hand to fold: against such a loose player it's never a guarantee, but if we can get them to fold any pair 44-JJ and any A/K-high hand that doesn't have a draw on this board, we deny a lot of equity and get to draw heads-up against SB.

And if we shove and get called, I believe we only need about 25% scoop equity to be GII good. If CO is only calling a range of (Q, KK+, dd) and depending on a reasonable guess for what SB might go all-in with preflop, we have at least 27% equity in theory, from what I'm seeing in PPT.

However, we could also check/fold or check/call.

Check/folding has its merits, though we're liable to be folding a TON of equity.

And there's a specific reason I may want to check/call this flop: CO, while not especially bluffy according to my read, had made a $250 river shove on (I may be slightly misremembering; it's hard for me to look up this hand being an Ignition/DriveHUD user) a 23463 no-flush board with T864 (and no missed flush draw; it wasn't really a reasonable bluff... they got looked up by a "gutsy" 57 to lose the $650 pot I mentioned). If we shove, we could get something like (A!Q!TT+!dd) to fold (and that's good re: getting heads-up), but if we check we could get something like that to shove as a significant underdog to us heads-up in the side pot. (Wishful as that may sound, don't forget that CO is pretty maniacal, so who knows the limits of their spew range.)

So yeah: I'd love to hear how folks think through preflop and flop. As I mentioned, the preflop situation is one I keep finding myself in (especially with 1-2 maniacs at the table), and I'm not sure if I'm playing it right. I've included a bunch of my thoughts on both streets... hopefully folks find this big PLO50 hand interesting.

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