I'd definitely put a 3bet in on the flop in hand 1 ... thing is, with your read on this guy he's already shown you that you can't really count on him to build big pots for you when he has the initiative. Secondly, I would highly doubt he ever folds to a raise after c/MR in this spot. As played I'd shove since he's shown the propensity to bet smaller w/ marginal/medium strength hands like top pair and to call them down regardless of the board texture. With the read we have, I think it would be kinda silly not to shove TBH.

Hand 2, how can you be nearly 3 buy ins deep with all players in the hand and not have any dynamic going on ??? My only concern would be the squeezer having a hand like AA that thought the K would scare away his action so he decided not to bet the flop. The BB is almost always gonna have a hand like spades 56 or 9T imo, so I wouldn't worry about him. Even if the squeezer does have AK, I don't think it matters because he has to fold to a shove, unless hes a massive station. Also, FWIW, if I were to bet out on this turn, it would be specifically for the reason of shoving the river assuming no draws got there. Otherwise I think a better option would be to go for a c/r on the turn--if someone has a set or a hand they are willing to take to the felt, it's very very unlikely they will just flat the c/r, it's more likely they will just shove over you right there because of how strong you will appear. So if they call and the draws brick off, I think you have a much easier river shove and can expect a fold quite a bit more often. And, if it checks around, no prob, we get a free look at at least an 8 outer and maybe a ten outer.