[Ryno]

Average live 20 players check-call/check-raise their big hands because other average 20 players call the raise and call the river and get shown 2pair+ and say "aw shucks". It's just not an effective bluffing line, unless you know your opponent is able to bet and fold on the same street.

In hand 2 you have position, you have a lot of outs, he could certainly fold 88,77,55 and it's reasonable to believe you'd wait until the turn to raise back with a big hand given the sparse board.