NL100z - Busted OESD - bluff or no?

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NL100z - Busted OESD - bluff or no?

Blinds: $0.50/$1.00 (6 Players) BN: $105.28
SB: $142.97
BB: $100.00 (Hero)
UTG: $132.09
MP: $304.69
CO: $162.35
Villain is reg.
Preflop ($1.50) Hero is BB with J T
2 folds, CO raises to $2.12, 2 folds, Hero raises to $7.50, CO calls $5.38
I flat JTs here almost always but once in a while I'll 3-bet it (ie. if I'm losing)
Flop ($15.50) 4 K 2
Hero bets $7.50, CO calls $7.50
I expect to get called on this flop quite often but I have decent blockers to the K.
Turn ($30.50) 4 K 2 Q
Hero bets $14.50, CO calls $14.50
Good turn card for me to barrel. 33-JJ are probably all folding now. Although I block some of the range I want him to fold (TT-JJ) my cards also block his TP type hands as well.

I don't block diamonds and I'm giving them good odds here. Maybe I should have bet slightly larger like $20,
River ($59.50) 4 K 2 Q Q
Hero
I think this is a bad card to barrel. AQ and QdXd are all in his range. Kx might not believe me with the missed diamond draw and still call down.

Only his naked diamonds are folding -- but the question is can I find a bet sizing to target this portion of his range? I think I will also get re-bluffed a % of the time too, making giving up probably best here.

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