Hand 1 I would push it to this guy do you have a range on him he could be calling your shove with AQ+ or AQs+ or he could have a PP he didn't want to lay down some people never learn to fold mid and low PP and they go broke becuase of it But I wouldn't be folding KK preflop to often unless I see the guy only re rasie with AA .

Hand two

I would rerasie him preflop then if he fires back without a shove I would call and if the flop doesn't spike an A or K I would send it in and hope he doesn't have a set or AA or KK other then that you did ok.