Hand 1: Opening with less than half the pot really smells weak here and you'll get reraised a lot I think, so I'd be more inclined to open with $1.25-$1.75. As played, I favor calling his reraise over pushing since you have an extremely strong draw in position against a guy who will probably pay you off since you said he calls too much. Also, since he calls too much, you probably have less fold equity than you think. Overall, the push might be +EV since sometimes he'll reraise you on the flop with air sensing weakness, but I think calling the raise has much better value.

Hand 2: Probably a tougher spot than I'm giving it credit for, but I'm pretty sure I'd fold here at 25nl, albeit I'm not sure I could blame a call given your description.