NL200 Turn overbet with OESD+NFD

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NL200 Turn overbet with OESD+NFD

BN: $206
SB: $228.96 (Hero)
BB: $148.19
UTG: $397.38
HJ: $180.20
CO: $168.56
Villain is 40/40 over a 15 hand sample. Kinda irrelevant.
Preflop ($3.00) (6 Players)
Hero was dealt A 7
UTG raises to $5, HJ folds, CO folds, BN folds, Hero calls $4, BB folds
My default here is to normally fold but I decided to flat given the open was to 5BB and BB is a fish. Is this reasonable? I'm not sure tbh.

Edit: 2.5BB not 5BB
Flop ($12.00) 8 9 T (2 Players)
Hero checks, UTG checks
Excellent flop, I plan on CR/GII because of our equity.

Is leading here an option? I feel villain will check back a lot on this flop and leading might get him to fold 6 outs. Plus I can balance leading here with weak pairs for protection and 2 pair/sets.
Turn ($12.00) 8 9 T 3 (2 Players)
Hero bets $18, UTG calls $18
Decided to overbet the turn in case villain is checking back a hand like A8/A9/77. I can still have a lot of value hands that are doing this imo.

I'm not sure if a normal sized lead would be better, or to try and go for a C/R again (but it's likely if he checked flop he's checking turn as well).
River ($48.00) 8 9 T 3 9 (2 Players)
Hero bets $46
When villain flats my turn overbet I don't think it's ever with a 9. Most likely he has a pair+draw himself (like JT) or a hand like AT/JJ that maybe decided to check the flop since he gets CR'ed here often.

So if I'm planning to bluff these hands out I think I need to choose a rather large bet size. Would overbetting again OTR work here? In the end I decided on a PSB.

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