Villain is straightforward ABC and on the nitty side, about 12/8/3 over a large sample with 60% CB.

I'm running my usual 15/12 and we don't have significant history outside of both being regulars.

He is a little short so effective stacks are $160, I cover. 200NL FR.

I have T9on the button.

villain opens for $6 in MP2, I flat, SB calls, BB calls

pot $22
flop JJ8
-- sb checks, bb checks, villain c-bets $15, hero raises to $30, fold, fold, villain calls

in retrospect i know the CIB was terrible since I would not play a Jack like that.

pot $81
turn 5
-- villain checks, me?

Obviously I need to raise more on the flop if I'm going to rep a J, but given I misplayed the flop is barreling here terrible? His range is probably 88, TT+, AJ, maybe KJ and I would expect him to slowplay a jack here and CR the turn.

I take my free card generally

i would check this aswell, no point in risking money on a draw when you dont have to, and he could be check raising you

You pretty much answered your own question.
cb and hit your draw.

meh, so you turned it into the limit free-card play. No big deal, take the free card.

I'm betting $60 here.

River intentions if we blank and he checks?

Cry and take your loss because there is no FE left.

well, if we b/c here our red-line can only go up so it is the best play

barrel

I agree w/ a 2nd barrel.

I think barreling is horrible here. WTF are we repping? Take the free card, hit your draw.

A jack or 888. There's 0 risk of getting check raised on this turn and I think we can actually rep a pretty strong hand. Against a nitty player I don't hate emptying the clip. It's not like we get his stack if we check back and bink off a heart or anything.

I'm assuming he will CR AJ or KJ in this spot.

if the 12/8 is opening KJ and AJ then good for him

59$/shove river. Be a man.

Results:

I bet $60, villain CRAI, I call, villain shows AJ, I brick.

eff stacks were 160?

idk then. flat flop is better

Check raising this flop looks weird if I am the villain. Why would you check raise on the flop here, is what I would be thinking.

If the villain is abc enough that he is not folding to a turn shove then check behind. I doubt he is folding if you get there on the river and shove. If you think you have any FE on the turn then jam away.

As played I think I check turn hope to hit the free card.

Take a free card.

I am confused. I always thot CIB = check it behind. Or does it mean creepy itsy-bitsy bet?

I would take the free turn card.

it means click it back