2/5: Is it necessary to cbet this board as preflop 3bettor vs a SB cold caller?

Checking or betting small both seem fine to me. If you think SB could be trapping with a monster, I'd rather check/give up. Otherwise, if you really think we have 2 overcards when behind, it can be OK to bet here (but even then we can mix in some checks). We don't need to empty the clip just because we bet once.

This is a good board to check back. You don't have the range advantage on this board (but he may not either), so checking is a valid choice unless you think SB will overfold here (you can clean up some equity that is not PPs).

I think it's very villain dependent (and if he has a fold button if you double or triple barrell against his 99 or whatever), but I do think in a 3b pot, he's going to range you as big PPs and big Aces, and by checking he might infer AK a lot (even more than villains do usually), so I lean bet, but checking is hardly horrible.

Yes, checking here assumes that you check some of your big pairs some of the time.

I would just range bet, your range crushes a fish here and AK gets called by worse a lot

Online a fish will be pretty wide here, I'm assuming fish aren't cold calling 3-bets way tighter live

Even if he infers AK a lot when we do check, he’s still not going to start bluffing with a hand like KQ, no? If he bets turn, he probably beats us with a hand like 99 anyway.

Are you continuing the aggression tho? If he calls a flop bet, he most likely has a PP, that would love to see a cheap showdown.

So make the showdown expensive.

This!!! Disappoint the villain!!

Would mostly bet flop small ($40 seems good) with everything, only reason not to is if he's going to x/r 99.
If nothing else betting flop small gets us to see all 5 cards cheaply.

I don't think piling money is good if he calls flop, personally. If he had $1k as well I'd consider it sometimes (apart from balance[1], I've unloaded the clip into 99 for 200bb enough times).
We don't win money by trying to bluff fish off 99 here for only 100bb in a 3bet pot. And if he's not a fish he can have QQ+.
Might go for it anyway if turn is a Q, but even that's not great.

[1] You have to be shoving at least JJ+ to be close to balanced if you go for it with all AK.

I like 1/3 pot on the flop. You can have the best hand sometimes and equity denial is helpful by getting him to fold hands that are behind but have outs. I wouldn't range a fish on just pocket pairs here. Fish will cold call with wide ranges, suited broadways, maybe even some offsuit broadways like KQo, suited connectors, etc.

If he calls then you can check back turn a lot. The 1/3 flop bet buys you 2 free cards. And you can always value bet if a K or A come out.

You can also barrel certain runouts like turn diamonds or turn clubs holding blockers to backdoor flush draws.

Is he really folding his overs to a 1/3p cbet?

C-bet 1/3 pot.

Maybe, maybe not. If he isn't folding overs, then we still get value (especially vs a hand like AQ that is less likely to stab later streets). We still can get him to fold on a later street. We may be able to call light on the river too. We can also get value when we hit.

In a lot of ways I think it is preferable to bet 1/3 p on the flop than to face a big bet on the turn and not get to realize our equity.