$100 NL 99 Set on Straighty Board

[toybux]

Villian could have a ton of hands here if he is at all agressive. The button raise is probably a very wide range. Hands like KT, K9 (unlikely with the case 9), K8, 78 (again less likely because the PFR probably won't slowplay this on the flop) are all possible holdings as well. He could even have picked up a flush draw to go with his straight draw (or even pair + fd) and decided to play back at you here for some reason. I think a push is really the only reasonable choice here, and I'd be feeling pretty good about it most of the time.

This spot actually seems like a check-raise is preferable to leading out. If we lead the flop, villian may call with a somewhat wide range. Overpairs will probably raise us, and maybe we'd get semi-bluff raised sometimes as well. If we just get called (by a one-pair type hand or a pair and draw), the turn is often tricky. Scary cards that complete straights can show up, or overcards that scare those one-pair hands. The straight cards can also scare two pair hands and maybe even worse sets (sometimes people will fold these hands!) Also, since we have top set, villian is very unlikely to have top pair, so instead has to have 2nd pair or worse. This makes it hard to get paid off on the turn by most any one pair hands. If villian has a draw and we pot it, we're not super-likely to get a call. Basically, for these reasons and a few others I'm not thinking clearly enough to elucidate, I basically don't want to play a turn here, so making some big big bets on the flop is very preferrable to still having thus much behind on the turn.

If we check, average villian will probably bet any pair he has, any draw, and a lot of air as a c-bet. Say he bets $4 and we check-raise to $16. Now, most of the time villian will fold to this (which is why this isn't really a bad spot to do this as a bluff either, which seems like it should be contradictory but I don't think it is) and we take the pot down right here. The hands that villian will fold here are complete air, 2nd or 3rd pair, underpairs. All of these hands are hands we would have had difficulty getting value from on the turn anyway, so folding them out after they have already put in a bet on the flop isn't really much of a loss. If villian has a hand like two pair or an overpair, we will get 3bet a lot here. People who raise on the button have a tendency to think that anyone playing back at them is FOS. Getting the money in on the flop here is good because it avoids any scare cards potentially scaring them into folding. The other advantage here is draws. Because villian put in the intial bet, we've now made a 2nd larger bet. This gives villian an opportunity to make a big semi-bluff with hands like AT/KT/QT/T8/T7/76 when they have the equity to feel more comfortable making the play. Because of the sequence of betting, we now put villian in a spot where making a big semibluff seems fairly attrative given that our check-raises can often be FOS on this flop. Getting villian to shove here with a pair + straight draw or just the SD would be really great, wouldn't it? I think that since the check-raise gives villian the chance to be the one making the flop 3bet, and since I don't think it loses much value from other hands villian could have, it is the superior line to leading out on this board. This isn't necessarily as clear as I would like it to be, but I think I can summarize it quickly: Its going hard to get value from any weak hands the villian has here. By check-raising, we let villian be the one to put in the 3rd bet and thus make it easier for villian to make a big mistake on the flop. We would like this hand to end earlier rather than later on this board.

Also, does anyone else think there isn't actually a contradiction between saying this is a good flop to bluff c-r and also that c-r is the best line for value? Maybe this just isn't a great flop to bluff c-r.

This is long and disjointed. Any thoughts would be appreciated.