You goal should be getting the most money into the middle in this pot. On the flop, the check call is fine, worse hands might fire again. On the turn, his weak bet is pretty much telling you that if you want money in the pot, you're gonna have to raise him.

Definitely check/raise this turn. As played, didn't his small ass river bet just drive you crazy? I would have had trouble flat calling anything in that spot, without raising.