re: Poker & $4 NLHE 6-max: Odd River Bet
I probably just fold pre to be honest. He is short stacked and you won't make a good hand very often (this isn't a good hand). You barely get paid off the times you do hit a nice board. Just not worth it.
As played it's a clear fold. What does he ever have here that you beat? Ever? Looks like he has a really strong hand and was afraid to raise the turn and have you fold but now doesn't want it to check through on the river. When you take a call/bet line like this, he isn't bluffing enough rivers for this to ever be profitable.
And to answer your question above. We want to bet big enough to make him make mistakes. By betting around 3/4 pot here, he isn't getting great odds
to call on gutshots or flush draws. But most will call with said hands, so that we make a killing in the long run when they brick so so often. We don't want worse to fold and we're possibly hoping that better folds such as maybe A7-A9. But honestly, your hand is pretty weak so meh, I think betting 2/3 here is fine and folding to any aggression, such as him betting pot on river lol.