Hand 1 for analysis

[sawseech]

you can stack him if you catch
call

[pyedog]

I would go all in here and try to steal the $55 already in the pot. You have 12 near lock outs to a winning hand if you are called. That's about 45% to hit, so assuming he even folds 10% of the time to your all-in then it's probably a +EV play.

EV = (0.1)*55 + (0.9)(0.45)*165 - (0.9)(0.55)*135 = $5.5

Considering he could easily be raising with overcards on this flop I think his chance of folding is higher than 10% too. Then again, this is a high variance play at higher stakes than I play at. Just calling and trying to extract value when you hit out of position would seem difficult. Plus he might just bet too much on the turn for you to call profitably (which seems likely from an aggressive opponent). In that case then you've wasted the $25 call on the flop.

Edit: math error in formula. It's closer than I first estimated assuming he only folds 10% of the time.