Online multitable tournament, during the rebuy stage before the add-on break
Blinds: 40/80, 10 handed table
EP 2, very loose passive, 46BB (3655), has played almost every hand out of the last 33 hands (27 of those, all limped), and has over valued top pair at show down
Hero, BTN, 64BB, AhJs
Preflop: EP2 calls, Hero raises big due to Villain being so loose to 400, EP2 calls
Flop: (pot 920, SPR 3.5 with 3255 left behind) 5sJhJc
EP2 checks, Hero checks (reasoning, unlikely he has the case Jack; there are only 3 fives in the deck so most likely missed the flop. Not sure if he'd call a c-bet with 66-TT; relatively low SPR vs 1 opponent who over values top pair, seems like a good spot to slow play)
Turn: 8s
EP2 bets 280, Hero raises to 600 with back door straight and flush draws possible, EP2 calls
River: (pot 2120, 2655 left behind) 4h, EP2 checks, Hero bets 800, EP2 calls
With this hand and board, I wanted to extract as many chips as I could from Villain's stack. Should I have played any street differently for better chip expected value in the long run? My biggest questions are: was my preflop raise too big, should I have bet the flop and should I have shoved the River as played?
Don