Well, he is not pretty good since he is calling you OOP. His range to defend is probably middle range, JT, QJ, T9... He is going to c/s those hands because he doesn't know what to do in such a draw heavy board. He can also have flush draws, I think you can never fold that flop, also you only need about 35% equity against his hand. Since you have seen him 3bet before he is very likelly going to 3bet AJ against a late position raise a lot of the time, so you are way ahead of his range.

i agree, he has been pretty happy calling with connectors..

what do you think about the first hand?

I am bad, I would probably get it in on the flop :P

That's exactly what I meant for the first hand !
Raise him and call or shove him OTF