H1: I was trying to get him off of his air/bottom pair/mid pair/bottom end straight draw hands, which now looking back, I don't see much of in his range. Should it have been a check behind, planning to check/fold the river, or bet 1/2 pot and check behind on river?

H2: Should I be giving him more like 22+, broadways preflop? If so, I can see him trying to bluff overcards on the flop, but not again on the turn? So, say he bets whole range on the flop, for value or bluffing, the only thing I see him firing another on the turn with that we beat would be 88-TT. Pretty small part of this range...