Hand 1: Using your range your a 54% favorite preflop, but you ship it when your equity is 46%. Looks like you don't want to gamble when you are ahead but want to gamble when you are behind.

Board: 4h Ks 9d

45.571%{ QdQs }
54.429% { 99+, AQs+, AQo+ }

Hand 2
Even if we assume his range is 99+,AJs+,AJo+ preflop, he isn't reraising here with anything but 99+ and even if a throw in aks your equity is 37% so you are calling 12.40 for a chance to win a pot of 16.40. Your personal equity will be .37*28.80=10.60. This is negative EV.

I don't play at your level but just a thought.