The more I think about it, the less and less I care about extracting thin value on the turn from his floating range. I feel like my best overall strategy against this type of player is to bet/bet/shove very often.

Someone who is trying to peel preflop too often and peel the flop too often, I can't see how any hand, even one without equity, is bad to barrel flop and any turn with... And also to shove river based on the card and his timing.

I think this strategy is superior to extracting thin value from his floats by trying to c/c or c/r some turns because I want to be 3betting this player with a very wide range. Clearly if we have 44/54hh and 89o it's hero's plan to be 3betting this ridiculously wide of a range as it is. If the hands we had to work with were more hands like KQ QJ JT AQ AJ, then I might feel like there is more value in extracting from floats.

If he is making the mistake of not ever raising the flop shouldn't we just apply maximum pressure and keep putting him to tough decisions until he adjusts, then start to mix it up once he finally decides to put us to a decision?

I don't see a difference between 44, 45hh and 89o given this plan.