[Yeti]

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How often do I lead here and win outright, or just get cold-called?

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You say it as if these are bad things. Like flawless said, what about next time you lead your flush draw/nothing, and he folds? Or just calls and gives you a nice 'free' chance to make your flush.

BTW, if you lead, and they have a hand they are willing to felt with, they will rightly or wrongly nearly always raise. Only the better players will call in spots like this, looking to get their money in in much better shape v your range on a safe turn.

FWIW, no, I do not think check-raising is bad. You have to mix it up now and then. Like everyone said, I would go a lot more, probably allin.