Thanks guys!
Well the consensus here appear to be that
I should have pot the flop or at least a bigger raise and then another bigger raise on the turn, which definitely makes sense to really force them to pay for their draws.
My thought process on the river was that any bet I am making would actually force B to bet. I
FEEL like if I had bet small (50ish), it either looks like an extreme "i have the nuts value bet" or a "this is a small bluff and please dont call".
He had previously bluffed on big hands on the river to try and just take pots when he felt he was behind, so I didn't really want him to pot it and just check it in hope he had a hand worth showing down but not betting. (He wasn't too much of a thinker and more of a thrill seeking gambler I believe)
The river went down like this: