Now the better hand reader he is and the more aware of what his perceived range is the more inclined we might be still to shove for value because polarising our range might be better because he never actually calls in this spot with a half pot bet..

I think calling AK here is pretty bad to a half pot bet.
Would we actually ever bet as a bluff half pot?
I think we have to bet full pot - to get called by bluffcatchers.

1/2 pot looks too much value-ish imo. So unless we feel it'll induce vilain to raise with made hands as a bluff, I don't like it.

Overbetting will look very nutty to any decent TAG without reads/history suggesting otherwise. OP admits that he would only shove with the nuts... so let's not give a too easy decision to vilain.

One thing to consider is that we can't expect to be bluff catched often as we are not repping much bluff no matter how much we bet here. We just don't have much air in our range when we get to the river this way on that board. I would just bet as much as I think sets or lower flushes would call ... prolly in the 55$-60$ range, maybe a little more.

I agree with this and I made a pretty big mistake by betting what I did, it was just so valueish (43$) and I regret it.
I think somewhere close to pot is better.
How about a slight overbet, something like 95$ ? Now this is something i'd definitely do with a bluff sometime or a whiffed diamond draw, it polarizes my range a lot.

*grunch*

Bet as much as you would with A2s ldo.

well the thing is, i really dont see villain ever bluffcatching here, not enough bluffs in heros range. hero Cbet flop 4way, barrelled turn hard and now if he pots it here i dont see how villain could ever put enough bluffs in his range to justify calling a PSB to bluffcatch. i think anything villain calls with are hands he thinks can win at SD, meaning they can beat some of heros value range. i think giving villain better odds to call here allows more of his range to call. not really disagreeing with a PSB, just the notion that villain will bluffcatch a PSB on the river but fold to a 1/2 pot because it looks too much like a valuebet.

Sounds like we've established ITT what an awesome bluffing spot looks like.

Sure, but would it be optimal to get to the river that way with air OP has in his UTG range?

I think he meant turning 33 into a bluff when I value bet the river to a normal size.
Pretty sick bluff, dont think a lot of people at 100NL would pull it

Would be pretty sick thing to do imo

The fact is, in this particular spot, you cannot ever have a bluff when you bet this river, no matter what size. So an overbet shove is the absolute worst size, as it is polarizing your hand to the nuts or air where you have no air and will never be called (if villain is indeed a decent thinking player like you say.) IMO you want to bet a size that looks like a flopped two pair, which will allow him to still call with better two pairs, sets, and raise with flushes. Slightly less than half pot seems pretty good, something like $28-34. Unfortunately if villain has AK or AQ you cannot get any more money out of him no matter what the size, and those are very likely hands given villain's line

I thought about it a little more ...

If we assume there is not much action to be gain from AK or AQ, shouldn't we be c/r'ing?

Or it's just too likely that he checks back sets?

I have outline the effects of card removal - you can apply your own set of conditions for his range.
Then look at what you think his river range is....

A reason to check would be if he was going to bet his entire range..
If that is not so - then by c/r we would need him to be bet/calling a decent portion of his river betting range.

If he is just ever bet/folding the river - then we should never check because - then it is more likely that he will bet size as thin value not to get himself pot-stuck.

Which is an excellent supplementary reason - why from an optimal bet -sizing proposition - that our bet should necessarily be larger than his bet if he checked to if both have = frequency.
Which it appears that OP believes to be true.

c/r would target his flushes ... if we bet say 55$ he might just call with his flushes but might call a c/r ... just some thoughts ...

I agree that if we check he could very well bet smaller than we would.

I think he calls flushes too - but I think he likely calls a shove if he has a flush.

e.g. whenever I have AK - so I have the nut blocker.
And I spazz monkey shove or check shove - what tends to happens - is that they tank and tank then usually call.

Which is what I would expect from a flush.
Pretty hard to lay down having chased poorly - hit your card then fold....