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If I thought for sure that my set was good on the flop, and you probably had something like top pair with a good kicker, or an overpair, I'd be very tempted to slowplay. Why not? A mega-raise there might push you out; but if you stay in, you've got essentially a two out draw. There's nothing else for him to fear on that board. Arguably he could have raised on the flop, but as far as safe poker moves go, slowplaying against someone with a two-outer is about as safe as it gets. I think the only hand he really has to worry about in that situation is pocket jacks, and that's less likely (based on the pre-flop activity) than a higher pair. Personally it looks to me like he just kinda got unlucky. In the long run you do probably make more money slowplaying the set on the flop and letting your opponent (especially if he's known to be aggressive) bet for you.
I don't have a fixed rule for trying to "bet someone out" when I put them on a draw. I think everyone who plays hold 'em understands the sometimes subtle difference between a scare bet and a bet you want to be called (no matter how huge it is). Against someone with four or fewer outs to improve, there's probably money to be made by slowing down. Against the more dangerous draws - flushes, open enders, or someone with top pair vs. your lower two pair - you probably want to get your money in quick and try to discourage them from calling. Sklansky would say the only important part is giving them bad pot odds on whatever their draw is, but the psychology of poker is such that sometimes, losing a pot you could have won by betting someone out earlier will cost you money - in the form of tilt, or just overly cautious play. Scared or angry poker is a money-loser, so you do what you have to to maintain that feeling that you can't be beat.
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