Did I misplay this river?

Magic 8 ball says “ask again later”

Should have jammed all in pre-flop.

Checking the flop is correct in my opinion. You are quite strong and safe and block the calling range.

However, after the flop goes check check, I think that you bet on this turn if only to prevent your opponent from drawing for free. As played, I would check raise all in on the turn. Remember that the later it gets, the weaker a set is going to be. Going all in on the turn is better than going all in on the river, generally.

The river, check-calling is probably best. Problem with going all in is that he can easily have flushes which will call, whereas he's unlikely to have an ace or better, which means that you only get called when you're beat and when he has that one ace. Instead, you should check-call and try to make him bluff.

A flop 1/3 C-bet then about 1/3 bet as well on the river is what I'd do. Maybe he'll pay us with a strong pair or the last Ace. There is no much reason our opponent can pay us often enough when we block everything strong and he almost never has trips or straights given the Preflop action. If he had the initiative and we just flatted the Preflop raise I'd be more passive and let him hang himself.

I suck but here is my play:

You both got in quite a damn bit pre-flop. You 4-bet, I would have c-bet on the flop with a bet to let someone like KK/ QQ/ JJ in his range go to a turn. Even if one of those hands goes to turns, maybe slow down a bit, to allow him to believe he has top set maybe and start building a pot. You block Nut flush, and for him to be pulling to the diamonds would be pretty ambitious I think, you have Ace blocker. So maybe he has AxKd or some pair with ONE diamond, and if he does, you still hold the Ace, so if he was thinking, the diamond draw doesn’t even really matter.

I would maybe check the turn, let villain stab at it, at this point if he did. I would be putting him on A5o at best, for two pair, could still be with any over pair as well I think.

River comes, 3 to a straight, villain would need a 2x to complete straight, given what’s going on, I doubt villain has a two based on pre-flop raising to a 4-bet, that would be pretty ambitious for a pre-flop raise to a 4-bet, I’m a loose player (fish) and even I wouldn’t do that. I would have bet small enough on the River to let at least a two pair in. I suck btw hahahaha so don’t take this as gold, I’m trying to get better.

Go down in stakes until you understand fundamentals a bit better