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It's 5 way, and we're first to act with what is very likely the best hand. This flop rarely gets checked through. If we bet we will be raised by strong draws, and better hands. There are lots of worse hands that will bet when checked to, but will only call if we bet. Checkraising here is an excellent way to get 2 bets in as opposed to 1 with a decent edge, and to buy some equity from draws that might call one, but not 2.
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Personally, I don't want to build a huge pot with a mediocre hand on a board with a lot of draws.
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It also gives us the option to fold if the action is really nasty.
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...or to get squeezed off our hand.
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In this case, we are often ahead of the bettor, and the 30/20 is raising almost every single hand that's ahead of us preflop, and raising lots of weaker hands on the flop, so he's not much of a parlay for 3town.
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I don't see why A6s, A7s, 76s, and perhaps 77 and 66 aren't all squarely in his range, even if he never overlimps with something like AJ. Plus UTG can have any of those hands. We aren't ahead of all that many A-x hands really.
Looking at some sims, if we're up against a weaker Ax hand and a good draw, our equity is good but not great, around 45-50%:
http://twodimes.net/h/?z=2506208
pokenum -h ad th - kc 9c - as 3s -- ac 6d 7c
Holdem Hi: 903 enumerated boards containing Ac 7c 6d
cards win %win lose %lose tie %tie EV
Ad Th 420 46.51 426 47.18 57 6.31 0.497
Kc 9c 363 40.20 540 59.80 0 0.00 0.402
As 3s 63 6.98 783 86.71 57 6.31 0.101
OTOH, if we're dominated, we're in quite a bit of trouble.
http://twodimes.net/h/?z=2506205
pokenum -h ad th - kc 9c - as 7s -- ac 6d 7c
Holdem Hi: 903 enumerated boards containing Ac 7c 6d
cards win %win lose %lose tie %tie EV
Ad Th 76 8.42 822 91.03 5 0.55 0.087
Kc 9c 332 36.77 571 63.23 0 0.00 0.368
As 7s 490 54.26 408 45.18 5 0.55 0.545
If you take sort of the weighted average of these scenarios, I don't see how we're getting much better than fair share here, especially once considering the risk of a 3-bet and that we have the first action on the turn if we want to re-take the initiative there.
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I c/r this flop 100% of the time, and think it's clearly the best play.
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Well, good for you. But why are you planning on check-raising? Because you hope the bet comes early in the field so that you can play a big pot? Because you hope that the bet comes late so that you can protect your hand?
Those are fairly contradictory objectives, and the thing is, in an unraised pot, we have no idea where the action is coming from, or even whether it's coming at all. It seems inherently wrong to me to make a play that could be an offensive check-raise if the action goes one way, and a defensive check-raise it goes another.