Hand 1:
Key here is making sure you get as much money as possible when ahead (since I think you're losing your stack when you're behind)
Possible hands for villain: overpair (88-TT, 36 combos), higher set (66, 77, 12 combos), straight (45s, 8 combos), straight draw (89s, 8 combos), two pair (67s, 4 combos)
My worry with raising all-in is that you'll knock the overpair out but leave the better hands in. The draw only exists and hits 4% of the time (and an overpair hits a set 4% of the time).
In the heat of battle, I'm pretty sure I'd raise all in, but as an alternative line, how about calling the raise, then betting say $30 on turn and $40 on the river? He may not be able to get away from his overpair.
Hand 2:
Yuck! I wish I knew what to do here
Check behind on the turn, and call any sized bet on a non-club river?
That way you might get bets from AK/busted flush as well as a set. If a club falls and he doesn't have it, he might check a set here fearing you do.