Playing Deep

[Spellmen]

This is mainly a hypothetical question because there have been times scenarios like these have gotten me in trouble. Say you and villain both have 5-8 times the buy in. You flop top set of, lets say kings on a K108 board with two to a suit. If you are in position and bet the pot and are checkraised by villain. In this instance, your read on villain is that this does not mean second set, he could have the straight/flush draw with JQ9A or even as little as open ender with flush draw or top two with flush. Another raise will only commit 1/4 -1/2 your stack in the flop. Do you repot it again or wait for a safe turn. Obviously if you wait you are letting him draw cheap, and its also possible he could bluff with second set if a scare card hits. How would a cold caller of villains checkraise change your decision. Does your choice change if positions are reversed and you bet out in EP and villain raises from button?

Given a 1 buy in stack repopping it and getting all in is an easy decision, but when sitting on a big stack I seem to get in trouble if I repop it then a scarecard hits, mainly when I'm out of position or in position and villain bets into me when an obvious draw completes