OOP against a tough player, should I be quick to give up in these situations?

Without looking at the specific spot, the answer to the question in the title is yes.

Now that I have seen it, yes, give up. On the flop.

Eastern european or middle eastern

I'm not sure which.
Dark hair, light skin.
Looks sort of Iranian, but his light accent sounds a little Russian.
Stocky, medium-long hair.
I imagine him to be a chess player (with no evidence), so maybe that accent is Russian. He was discussing hands with his neighbor again.

PRE - looks fine.

FLOP - HU and OOP, I'm mostly just range checking flop, unless I see a reason not to, and I don't see one here.

Our hand has enough going on to check-call a reasonable sized bet and continue across a lot of turns. But I don't think we want to start building a big pot yet. If the flop checks through, we can look to make a delayed c-bet on a lot of turns. If V bets really small, maybe occasionally we put in a check raise. But mostly I'm just check-evaluating.

If we do bet, the size I choose is going to be heavily dependent on board texture and our hand. I think we'd bet small if we think we'd be doing a lot of c-betting here. When you bet so large, I'm not sure what you're repping. We could have 88 and over-pairs, but that's about it for value. When V calls, I'm concerned about how much money we're committing with just two overs and a backdoor wheel draw.

TURN - the 2h is basically a brick, but does give us the inside straight draw. Not enough stack depth to bet again and leave a chunky bet for the river, so either check, or jam. If V is a thinking player who can fold 99-JJ, I'd probably jam. Otherwise I'd check and probably fold if he bets.

Oooh, maybe a Chechen? (John Wick music intensifies...)

Anyway, I like the 3!, like the sizing, cbet on 843r, maybe, but definitely not for 2/3. What in our 3! range feels like it needs to lead for so big? JJ-88?

What do you think V's calling range is after that, considering V perceives you as decent and thoughtful? My guess is it's a lot of medium PPs that didn't want to 4!, along with some larger Aces, KQs??. Maybe AQ+? Most of this beats you like a gong.

Normally, if we wanted to rep AA-QQ, we'd be looking to pot control the turn. Now AP, I think we lose if we go x or x-c, river bet or x-c 33 to 50. Would you play JJ-99 with an overbet shove here? Or instead look like you're going for 3 streets with bet 30-40%, 110-140 or so, shove clean rivers? V is studied, so will V fold AQ+/KQ, even some PP if you do this, and look like you might be milking V?
(Edit, obv we beat KQ; just trying to be complete with V's range.)

When he calls my large flop bet, I am thinking his range has a lot of PP's and not alot of A/K high.

One third on flop with the overs and backdoors. Size up on turn with the gutshot

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Yes I would try to avoid playing bloated pots OOP against a strong player.

I will employ a 3! or fold strat from the SB but I’m not married to it. I think we can have some flats including PPs and some suited Broadway. I would much rather flat AJs and 3! AJo. 3! here is obv fine though and sizing is fine.

OTF we need to have a plan. Checking and betting both have merit but here is what I don’t want to do - c/c with this hand. BD equity does not serve us well without the betting lead. If I am betting, I would bet small (1/4 to 1/3) with essentially my entire range in a 3-bet pot. I will fold to a c/r. But my plan would be to barrel a lot of turns large. Betting flop large strengthens his range and we basically have to give up on most turns. Bluffing him off AK/AQ and some pairs is going to require 2 (or 3) streets. So buckle up or just c/f flop.

I might check/jam depends on how sticky and aggro he is.

If he is on the more passive side probably just check/fold.

I check or bet large OTF. Checking about 60-70% of the time. Trying to mix between my overpairs and naked overs. We want to be able to bomb this flop with AA and get the maximum from weaker overpairs. Its very player dependent - how sticky is he? You say he can make a good fold and sees you as tight? If you bet 120 you have 500 behind and can shove turn for a little over pot. I'd probably bet 120 OTF and then shove any ♠, A, or J. So that's 16 out of 47 cards or 34% of the time. 2♥ is maybe not bad to shove on either we pick up a sniff of equity.

You actually might be able to just call pre here. Yes, the book does say 3 or fold. However, a big part of that is the aggressive players behind you will squeeze when you flat.

If you have 2 omcs behind or others who never squeeze you can call here. Raising is fine too.

Also, the solver is a solver. So it isn't really worried about things like being Oop against a guy who might be a better player.

Anyway, raise is standard and I usually would but you are free to adjust for these live dynamics. It's also a bit deceptive to have a big ace here.

If you do raise, I would size up a bit for the same basic reasons. I want to charge him to use his skill in position. Plus my hand is pretty happy to win now.

Yes, flop is a small cbet imo.

Having bet so large, I think you're probably just done betting. Any decent reg knows your aces now have wheel draws and will not consider folding a pair.

You aren't deep enough to run him off tt or something. I would check

You can check fold. Maybe call a tiny bet. Hope it goes check check. Maybe bluff a king on the river in some scenarios.

Results:

Bummer it didn't get through. I can see why V tanked for a bit though. Guess V thought you didn't have that many higher PP that would play it this way.

I wonder if x turn (hoping V x-b), and then betting >3/4 on the K river might've gotten a fold? At least you chopped, and we all got to learn a little along the way.