I'm not entirely following you here. The only thing I do think I understand is the raiser who has middle set.

I think one very important question here is just how many cards on the turn are bad for you if he's on a draw. Or is the idea this: Regardless of how draw-heavy the flop is, you just check-call, and that's probably going to be close to stack anyway. With your check, you've in any case repped that you missed your draw if that's what you were on, and you always have outs with your set.

If that's the idea, then do you check-raise a passive bet or just call him down? Also, what if the guy is over-cautious and won't bet into a non-blank turn with his middle set?