1- I like the idea of betting and playing our hand as a bluff. On the turn we can barrel any A/K/J/T/9/8 quite happily. I definitely agree that betting flop small to exploit his floating tendancies is the way to go, particularly since this villain is not going to raise us here ever.

2 - Definitely bet, there are even more great barreling cards here - any A/K/(T)/9/7/6/5/4/diamond is going help our hand or weaken his range vs our range - over half the deck

3 -Surely it is not a mistake to have some sort of c/f flop range vs. someone who is going to be floating a lot and generally trying to own us. 44 in particular is really weak and has very little chance of improving on the turn. This is why I hate 3betting small PPs unless I'm going to shove over a prolific 4bet bluffer.

4 -

If you check and call his turn float bet after your flop cbet, you are unsure of how often he will follow through on the river.
I think this is the key point here. We're going to look weak on a lot of rivers and I think he will vtown himself sometimes and also bluff a lot. I think bet, c/c c/c is best here, I imagine most of his 3barrel calling range (Qx/AA/KK/sets/random two pairs) is going to bet the river for value and he can have a large bluffing frequency.

5 - I think is close between c/f and bet. If we bet I think we're going to have to follow through on some turns where we have no equity whatsoever agaisnt his range and don't help our range that much (thinking of like J/T/9) and I don't know if that's a good plan. I probably c/f.