two 2-5 hands at the Mirage against a weirdo

[anduril]

Weird guy with sunglasses and hat sits down about an hour ago, seems tight, already min-checkraised the flop with a set vs a clear overpair. I'm chatting with my friend at the table who is making 6 out of every 10 hands $15 to go and getting away with it. I haven't had any hands to play since he sat down due to the new "blind" being $15.

hand 1: I($600ish) open to $15 with KK, weirdo calls in SB (everyone is coldcalling $15 because of my friend's donkeyness).
flop is J 3 2r

he($550) checks, I bet $25 into a $33 pot, he checkraises to $75. I get the feeling it's going to cost me a ton if he has a set or AJ, so which do I put him on to save/earn me money? If I call the c/r he's definitely betting $100 or more on the turn, regardless of what it is. So now what?

hand 2: Several hours later, both our stacks have gone up/down. I ($600ish) open to $15 with J9h, weirdo is now in BB(has me covered) calls.
flop is 9c Kc 8h
He bets $20 into me, I call
turn is 10d, he checks, I bet $45, he checkraises all-in. Check thru the turn?

[Richie Rich]

** Bet the first hand. Strongly doubt he has you beat.
** Fold the second hand. Even though you picked up a draw, it's not worth chasing.

[scdavis0]

On the first hand, call the check/raise, call the turn, evaluate river.

[anduril]

[ QUOTE ]
** Bet the first hand. Strongly doubt he has you beat.
** Fold the second hand. Even though you picked up a draw, it's not worth chasing.

[/ QUOTE ]

I did bet the first hand, he raised.

I did fold the second hand, my question is should I have checked through the turn instead of trying to take it down there?