Button ($700) - Black 40's, dressed casual wearing a trucking company hat. He owns the company. Seems like he was at the casino to have fun and is on the tail end of an all-nighter. Joking around a lot. His play is erratic but mostly loose. He will get aggressive when facing weakness like when checked to, but hasn't been 3betting light or making big raises as bluffs or semibluffs post flop that I have seen. He has done a blind raise to 20 preflop once. He also shoved 400 from the SB over 3 limpers (you read that right!) saying it was easier to get the hand over. Two potentially relevant hands: He tried to bluff a missed flush draw OTR versus a TAG who bet flop and turn and was looked up. He limped K2o in LP and checked top pair on the flop.

Hero (covers) - White 30's, dressed casual, no headphones. Came from a broken table about an hour ago and been active preflop with raises (table was passive and got good spots). But hasn't played many interesting hands post flop if button is even watching.

Preflop: Hero raises KcJc in MP to 20. Short stack calls HJ. Btn and BB call.

Flop ($80): K 8s 3. BB checks. Hero (mis)reads the short stack for shoving his last 60ish which he had been doing wide and checks to get effective last position. But it checks through.

Turn ($80): K 8s 3 Ks. BB checks. Hero bets $65. Short stack folds . Btn says "why so much I had 35 ready?" Then calls. BB folds.

River ($210) K 8s 3 Ks 8h. Btn has about $600 left. What is hero's best line here? Lead and for how much? Or go for check raise of how much?

Bet, after turn complaint it is too likely Btn will check behind if you check. It is very unlikely your going to get raised unless it is a chop or he happens to have 88. I see two ways of betting this depending on what you put villain on. If think Btn is weak, go $50 to get a crying call from pairs over 8 and AX hands that might be hoping for a chop. If you think he has a strong hand then go $150 to get a call from 8X hands.

I'm smelling weakness also. Bet 50-75 and see if you can get a sigh-call.

Without posting results, I will say that I actually did lead this river but now think it might be a check/raise. Before I post why, any thoughts?

It is a c/r bc that is how you maximize your value against his range.

i.e, unless he's a total drooler you are only getting maybe sigh called by an 8x. Kx you are chopping so that's not a consideration.

But there's a missed flush draw out there also. This is calling $0 but potentially betting a decent amount, unless he's really that passive.

8x is also probably betting when checked to.

So yea pretty clear check imo.

To top it off your line will look totally FOS, lol. Always great to look cray.

1) because he was floating you and folded
2) because he had an 8 and was betting
3) because he had a K and, advanced as you are, you were trying to get him off a chop by repping 8888. unfortunately it just increased the rake...

betting is >>>> than checking, villain almost always has some showdown value and is happy to check behind but might call a small bet. checking is just FPS and leaves money on the table long term.

edit: didnt see the fd, makes this a little closer. also his small pairs now got counterfeited, which makes a check reasonable.
still thinking betting > checking, but i downgraded from >>>> to > lol

V - late into session, has bluffed OTR, appeared to be weak OTT.

Hero has little postflop history, which could be read as vulnerability if you check.

Betting $130+ will fold missed FDs, part of his range (turn weakness). Likely will get a lower boat to call.

Checking will likely ensure the lower boat bets, besides the FDs.

given the board texture check here. don't really see much value in betting

Results:

Hero bets 150 and Btn folds the missed nut FD. I thought he would pay off this bet if he had an 8x hand. However seeing his missed FD got me to thinking I should've attempted a c/r and posted to get thoughts. Checking may induce a bet from missed FDs and other random junk that gets to the river like PPs since my c/b/c line looks weak. He probably bets 8x on the river and might pay off a c/r with my weird line. If he has Kx or 88, it doesn't matter what line I take. The downsides I see to the c/r are that he may sometimes check behind 8x or he may bet a smaller amount that I would've led and ten fold to a c/r sometimes.

Close but I prefer Chk over bet
1 he def bet 8 for value
2 maybe betting mid pair such as 99 1010 for value when Chk to him
3 now betting small pairs to bluff
4 bet missed flush draw to steal
Almost always no king