[Mattafuga]

I don't get it... If I was villain, I am confused as hell. So confused I'm calling you with any pair whether it be top, bottom or pocket.

If he loves to bluff checkraise, and you felt you could make the bluff this hand, I would continue to represent strength throughout the hand. I would bet the turn and river, and if he checkraised the river I would 3 bet it and use that as my bluff if I felt this was the right hand. Yeah, it costs 2 more bets, but it wins 2 more if it works.

And I think that that bluff would work more often than the one you attempted in that position against that villain.

Not to mention, are you sure that was the right spot? You said he checks and calls when he is strong, and bets and checkraises when he is weak, so according to your read, he is potentially showing strength throughout the hand.