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And lastly, there is always a chance the raiser will have a hand like KK on that Ace high board, and make a bad fold.

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You see this often at 100/200 in a 3 way pot with a button raise? I assume you are talking about them folding the flop or else I think it gets expensive to check/raise flop and bet turn. Is that the line you are going if you get it HUs or not on the turn and are called on the flop?

I just don't like the situations where we get 3 bet on the flop and then call the turn which makes our draw expensive or where we get called on flop and then raised on turn which makes our draw even more expensive.

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If I checkraise the flop and the middle guy folds and the button just calls, yes I will bet the turn here 100% of the time.

If I checkraise the flop and the middle guy calls and the button calls, I will give up the initiative and check/call the turn(the play is ruined cuz the Middle guy called)

If I checkraise the flop and the middle guy folds and the button now 3 bets, again I will give up the initiative, and usually check down and hope to hit my hand.

By the way I dont mind getting 3 bet when I have a hand as strong as a flush draw or OESD. Does this cost me in the long run in this situation? Sure it does. But this is just an annoying little cost in the long run sine my hand is strong enough to stand this pressure. No strategy is perfect. Every stategy has its risks, but the reward is winning the pot, and the hero doesnt have to take down many of these pots without the best hand to make up for these annoying little risks of being 3 bet or having our turn bet raised. The key here, is that since the hero already has a calling hand, he is really not risking that much by taking the initiative in this hand.