Hi man, good that you're trying to learn. I can definitely give you some pointers as well. Don't let my post count fool you, my older account is banned.
Make sure whenever you make a post like this to post the buy-in level so other members have an idea about the strength of the player pool you're playing against. Also add how you perceive villain to play, such as passive (lots of limping and check/calling), overaggressive (a player that fires away in every pot he plays), etc.
As for this hand:
Preflop:
Raise to 3.5x or somewhere in that neighborhood. Villain limps in what is presumably a low buy-in game, which means 99% of the time he's a recreational player. Your range is stronger, you can isolate the recreational player and you're in position. Your hand plays fine against a 3bet anyway, so that's not really an issue either and at a lower buy-in level there won't be a lot of 3betting anyway. You also mentioned you played your last three buttons, which is actually a good thing here because it make your perceived range weaker than your actual hand is. There's really no reason to do anything else here and it's actually the type of situation that you would want to wake up for in the morning as a poker player.
Flop:
Villain is probably a recreational that isn't a very thinking player, so I wouldn't narrow his range down to straights, sets or air based on his sizing. For one, only absolute tilt monkeys overbet a coordinated (read: drawheavy) board here with air against three other players, so I would exclude complete airball bluffs. Villain probably bets a strong 7, some small overpairs, strong draws or occasionally a set with this sizing, even though it's bad. When he bets 300 there's 526 chips in the pot and you have 1594 behind. Shoving can't be bad based on the money that's already in the pot and the equity you have against villains perceived range. Calling is okay as well. I would probably shove as villain likely pushes you off of your equity on the turn when it's not a K, Q or diamond. Based on his flop sizing the chance that he pots or overbets blanc turns is high from my experience and then you can't really call. Folding two overcards and the 2nd nut flush draw is a lot of equity being denied by a range that consists of some hands that we're a small favorite against on the flop, like the 7x hands and small overpairs. Sometimes it's best to just look at what's already out there and make your decision based on the fact that there's over 30% worth your stack in the pot. Would be player dependent and stakes dependent for me though, wouldn't take this route if I believe I have a huge edge in the field I'm playing against.
Turn: Just bet small to keep him in the pot with his pairs + weak diamond draws. It's presumably a lower buy-in level so you just want to bet your valuehands. You can suck him in with a smaller bet to make sure he calls with the range we described. You probably don't need to be very balanced against this specific player. Size up the river shove, which can be done with a smaller bet on the turn as well, and jam river.
River: Totally fine man, just an annoying cooler. Those happen sometimes, don't let it bother you.
Happy holidays!
Last edited by OG_Tuff; 12-24-2018 at 06:58 PM.