Live 2/5. Villain is a fish and hasn't played a hand in a few orbits. He is not a deep mathmetical thinker.

Effective stacks $550

Hero raises EP to $25 with KK
Villain, two seat away makes to $100 to go.

Back to Hero..

A) Ship
B) Re-raise to a $250-275 amount to commit Villain?
C) Flat

Remember villain does not think deep. As in, hands that would get scared by a shove might call a click-back.

What are the mathematical implications?

Like, by 4betting small, we are GII on any non-Ace flop anyways, and getting paid by TT-QQ type hands anyways as long as they're overpairs. We might lose some value if the flop is scary.

Of course given that we ship, that villain folds some of the AX hands, we'd like to keep villain in with AK, AQ as we are only fading an Ace on three cards (about 16% likely).

Thoughts?

I probably go like $225 I guess. [EDIT: If he'll call a little more near 100%, then go a little more.]

It is kinda funny and weird to think about. At these stakes online $100 is usually around the 4bet size, not the 3bet size (the open and the 3bet are much smaller of course).

4betting to $225 is kinda dumb cause if villain shoves, you're getting almost 2.4 to 1 and cannot fold basically anything, so you can't 4bet bluff/fold to that size. But most live opponents don't really think about this.

They really don't. This other hand I have AA in the BB. Villain raises to $25 MP. I make it $75. Villain 4-bets to $175. I click-back to $375 with $265 behind. Villain flats.

Flop 862r. Hero shoves. Villain FOLDS (???)

Some Villains will indeed stack off pre flop with AK, but after putting in half their stack fold the flop if they whiff.

We ought to make the play where their mistake (if they make it) costs them and pays us the most.

Sounds like our Villain here might stack off pre. But that is read-dependent. Do we want a larger chance of getting half a stack committed or MAYBE a lesser chance of getting a whole stack committed.

YMMV.

There really isn't much difference between shipping it and and raising it to 225 + committing on any flop.

I prefer shipping it though.

Do you want to be able to ship it with AKs aometimes with these stack sizes and get folds from e.g. JJ/QQ?

That would be another reason to ship IMO.

What are we doing with JJ and QQ in this spot?

Easy ship vs fish. He will call with AQs - 1010+ for sure and we will get full value vs these hands pre-flop. If we'r flatting we lost value on bad flops for him, and give him a chance to badbeat us with underdogs, cuz we should push 90% flops anyways.
JJ,QQ same.

Villain had 77, the 8 scared him.