Re: When to check-raise?
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1) family pot and the guy to my left is the preflop raiser and hence likely to bet the flop and I hit a set.
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Yes. Makes sense if you are likely to get calls between you and the original raiser.
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2) heads up and the pre-flop raiser always makes continuation bets and I've got a worthless hand on a scary all-low-cards board.
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Not sure about this. I've done this sometimes and it works rather often, but when it doesn't you lose a lot. Say that the pot is 1$. If his bet is potsized (1$) and your raise is also potsized (4$), you risk 4$ to win 2$.
You probably don't need to raise that much though. A minraise to 2$ woud get called to often, but maybe 3$ would be a good amount? Still you risk 3$ to win 2$, so this play has to work at least 3 times out of 5...
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