1/2 game, full ring as I and two others just joined table from another that broke up. Prior history with Vil2 (nut-peddler). Never seen Vil1, but he's a 70ish crazy-looking guy with ridiculous huge sunglasses tinted yellow (not transitions lenses but like something my 15 y.o. cheerleader cousin would wear). He's seemed to play fairly loose-passive, with occasional overbet on unraised flops being his only questionable moves.

I've sat 2-3 orbits at this table. First hand after sit down I 3b JJ and take down a reasonable pot pre. I raise a couple more opens and took down one more pot with a cbet leading up to this hand.

I'm in the #9 seat, Vil in the #1, so I have had to lean in to see him and obv haven't seen much of his face.

Stacks:
Vil1: 300 (SB)
Vil 2: 200 (UTG+1, first after straddle)
Hero: 400 (BTN)

$5 Straddled, Hero with 810. I call, and we go 5-way to the flop.
810Q (Pot: $25)
Vil1 is first and he bets $7, Vil 2 calls, couple folds around to me and I raise to $37 total.
(Thought process--the nearly pot-sized raise was intended for Vil2 to chase off all but a monster combo draw as I felt confident HE wouldn't call with just a gutter or some nonsense.)
Vil1 calls, nuttpeddler folds.

Turn: 2(Pot $106)
Checks to me, bet $50. Vil1 rapidly calls.
(Though that may be too thin to absolutely price out combo draws, he called so quickly that I think a pot-sized bet would have had exactly the same effect. I haven't seen him show down a hand, but his insta call makes me discount the probability of TPgk. I'm now thinking more about the flopped straight in his range).

River: 9 (Pot: $206) (sick)
Vil1 leads out for $110.

Hero ?
[Analysis of hand to date is appreciated: anyone size the raise OTF differently ?]

Fold preflop. Flop is OK. Bet bigger on turn. Fold river.

Either fold pre or bet pot on turn IMO.

Calling w/ 8-10 off this is a very favorable flop for you. You are only behind to 10-Q, J-9, or any of the 3 set possibilities - two of which are very unlikely, as he'd probably raise with 1010 or QQ in the sb.

Your bet on the flop was good. The turn is a complete blank and he checks - time to bet the pot. I'd even consider a shove on the turn. He could easily have both flush and straight draws, possibly also a piece of the board. I would look to end the hand right there as you are most likely ahead and if not it's a cooler.

As played, fold the river. Too many hands in his range which you are now losing to.

Tom- do you overbet or shove the Turn and why ?