25NL - 4 bet pot facing all in raise on the flop

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25NL - 4 bet pot facing all in raise on the flop

BB: trugrindr: $31.84
SB: Mushmellow: $33.72
Villain has been doing these weird min 3 bets with 30% frequency. I even saw him do it with J3o.
Preflop ($0.35) (2 Players)
Mushmellow was dealt 5 6
Mushmellow raises to $0.40, trugrindr raises to $1, Mushmellow raises to $4.25, trugrindr calls $3.50
I 4 bet bluff with 56o (he did it a bunch of times in a row so I needed to do this to counter right? maybe I should have chose a hand with blockers?). I expect him to shove or fold but he ends up calling. Isn't calling 4 bets OOP generally a bad idea unless you are trapping with really strong hands?
Flop ($9.50) T 4 3 (2 Players)
trugrindr checks, Mushmellow bets $6.50, trugrindr raises to $27.09, and is all in
I set up my flop bet to set up stacks to semi-bluff jam the turn if I get a good card to do this? What are some good cards I should jam turn on? Is this even a good line?

As played, he shoves my raise so I don't get a chance to follow through with my turn jam plan. My thoughts when facing the raise are:
-pot odds are about 32% so I need this much equity to call
-I have 8 eights and i pretty much lose to any other hand he can have if I miss because I only have 6 high
-part of his range includes flush draws that are higher than 6 high, I have to discount some of my straight outs then because against his flush draws not all my outs are clean against his flush draws

I end up laying it down, but feel like I made a mistake somewhere along the way because it seems like I put myself in an awkward and close spot. Should I check back instead on the flop?

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