I was playing villain on multiple tables were I had position on him and kept 3betting him a bit and annoying him preflop. We haven't tangled yet postflop though.
On this table I was relatively new and running around 23/17, mabybe a bit looser.

Party Poker, $0.25/$0.50 NL Hold'em Cash Game, 6 Players
LeggoPoker.com - Hand History Converter

UTG: $49.25
Hero (MP): $50
CO: $56.95 (23/15/1.3 over 321 hands)
BTN: $62.55
SB: $50.25
BB: $29.90

Pre-Flop: Q K dealt to Hero (MP)
UTG folds, Hero raises to $1.50, CO calls $1.50, 3 folds

Flop: ($3.75) J 3 K (2 Players)
Hero bets $3, CO raises to $10.50, Hero ?

Given that you have Kh and a Q here, I think you can make a call here, OOP, and then see what happens on the turn. The problem, and this is a leak for me, I have no idea what to do on the turn here a good % of the time. I can't let it go just yet because I think he may find an RR here with some draws trying to take you off the better hand - which he probably perceives to be wider than just Ks here.

I just 3bet here to $25.75 since the board is so drawy and you're OOP. Basically he's repping 33 and KJ, and heart draws - you've been pounding on him so he's probably looking to semi-bluff you with a high frequency here.

This crossed my mind, but I thought calling here would be the worst option making the rest of the hand as stated very very hard to play, note what the stacksizes are going to be if I called.

Do you know his raise cbet%? Have you seen him raise the flop much before? Have you seen him show down any draws yet to get an idea of how he plays draws?

If your read is just that you think he maybe he wants to play back, I would just fold this. It's a touch weak, but if you continue you're playing for stacks. Calling this raise and folding the turn is pretty gross. I hate stacking off with a marginal hand against two pair here because I thought maybe he wanted to make a move.

Perhaps he thinks you're a monkey and is just looking to make a big hand and let you stack off light.

Again, though, with any read at all on his cbet raise % or his habits with draws in position I think the argument could swing to stacking off, as his value raising range is relatively narrow (33/KJ/preflop slowplayed JJ/KK/AK).

Is villain a regular? Do you have stats? Is he aggressive?

Folding is not a good option imo. This is a drawy board, 33 and KJ are the only hands that beat you and his CC range pf is very wide given your opening a lot of lp and you have been playing together. its close between 3b and call, c/r turn. if the board was a lot drier i would flat call and c/rai the turn, but here i would just 3b to 25-28 and hope he shoves. flat calling and c/rai turn is cool but there are going to be a lot of cards that may scare you and he might check back to see a free card with a OESD or something

Villain is a regular, stats are in OP and we haven't played a big hand postflop, raise cbet% stat I don't use and should not be relevant I think due to the fact this hand is opponent specific(might not raise cbets alot normally but against me maybe a bit more).
These spots are akward because villains could be playing back at me, or waiting for a big hand to trap me since I've been playing aggressive and would probably spew here like you said.

This is a fair analysis. I don't think you should necessarily call the raise only to fold the turn, however.

A lot of this really does come down to flop reads. pf wars is one thing, but if he's solid, his range is really geared toward flips and hands that crush. Folding on the flop isn't awful here, but I think he's drawy and may do some things on the turn that makes getting involved in a 40bb pot with 80bb left OK.

You have the Kh and a Q, which means that the turn can sometimes be OK for you to chk/shove or c/c leaving you 50bb with some equity coming up on the river. So I don't mind seeing the turn here and re-evaluating.

Meh when you flat this the pot is 25 with 38 back.

You're going to be getting owned a ton on the turn.

What do you do when he bets a blank? Ship it in? If you're hunch is he's trying to semibluff or stone cold bluff you here because you're tilting him, he's likely to fire again? What do you do when he bets a heart? You have top pair and the 2nd nut flush redraw, so it's not a clear fold there either.

Even if he checks back the turn and the river brings a heart and he fires as a bluff, it's hard to call.

There's a lot of things that can go wrong, and basically when you flat this you're just sort of hoping he checks back a turn brick and checks back the river or bets at a brick.

I understand it's possible his range is wide and we have a strong hand and we don't want to let people run us over and all those things, but I just feel it's going to be hard to play profitable poker when you continue with this hand with the limited reads we're working with.

It sounds like this guy plays pretty tight and ABC on the whole, and you're been running him over a bit. What's your general game plan to make money from this guy? Is it to 3bet semi-light and take a lot of small pots away from him with aggression, or is it to make big multistreet hero calldowns with marginal hands?