When to check raise?

If you put your opponent on a weak holding, assuming heads up play...do you check raise on the flop or wait till the turn. I guess it depends on the type of opponent, but from experience ive found most ppl will call the c/r on the flop with overcards, but not so much on the turn. Has anyone noticed similar results?

Also, if you flop trips from BB when checked around (ie: you hold K8, and flopp comes 8 8 J) do you c/r on the flop, or turn? and when do you choose one over the other? How many players should be in to make the c/r on the flop worth it.

Thanks
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