Hand 1) What does his pre raising range look like?
What has villain been re-raising you with? Air? the nuts? Do we not know? It looks like you have position on him so is he check raising a lot?
Does he have any hands that pickup a combo draw on the turn?
calling 200 into 500 is close I think. Wish I could offer more advice
Hand 2) This is gross. 3betting the checkraise when the flush hits is super strong. I imagine he would raise the flop for protection with a set or two pair. Im all for ranges but I have to believe the only hand he can do this with is J9 as sick as that sounds.
But I suppose after putting half of our stack into this pot we can call ONLY (and this is important) if you really believe this guy will shove over your checkraise with an inferior hand.
PM me the results of hand 2!