Preflop is fine because you probably aren't getting squeezed, you keep in villain's dominated Kx and they appear to have some postflop leaks.

It is definitely close (we wouldn't flat with K9o and would definitely at least flat with KJo). Rake is a concern though...

The problem is postflop because you are making a play without any equity.

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Fold preflop.

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Pre call is really bad, flop call is bad, turn check raise is even worse than the call pre. Nothing about this hand is justifiable by the reads you Have.

I get the pre-flop but can someone explain the postflop.

You have a guy c-betting and double barrelling way too much.

He often has nothing on paired boards and c/r gets a lot of credit in the player pools.

Also saying you have no equity is a bit naive. If someone calls your CR here, they typically have a 1 pair hand or broadway, some of the more adventurous have Ax.

The question you're going to ask what do I do on rivers? I think check everything that's not made to him. We don't have nor will probably ever have enough history for him to exploit this. Even check any pair I made on rivers. You can make an argument for betting but what size...we might get bluffed off some %.

I am normally of the agreement to play as many hands as possible vs fish...but that's in position. This just seems bad on all fronts. Your reasoning for playing the hand (the cbetting/double barrelling too much) just means it is near impossible for you to realize any equity. Why not just take this line with our good hands instead...if you have a sb calling range pre, this is probably the literal worst hand to do any of this with.

You don't have a big enough sample to be sure enough about this to make a big adjustment

Possibly, but depends on the player and his perception of you, if he thinks at all he'll see you don't rep much.

Having some equity is a backup when your bluff fails, not sure how it's "naive". It just means your bluff has a lower fold threshold to be +EV.

This is all stuff that just eats into your EV.

In terms of the maths - I don't know exactly what your range is here, but it feels like this is one of the worst hands in it, apart from the blockers. Even if he is betting too much (and he should bet a lot), you can't profitably defend every hand, he just has too much range advantage given you capped yourself.

i have a feeling this is a level

If it is, then he's spent 500 posts setting it up.