Hand 1 I'm most likely check/folding this flop. Three villains in the hand, you are OOP to two of them, you have bottom pair with backdoor straigh and flush draws. I can't see a good reason to bet here, especially half the pot. If you want to bet i would bet full pot.

Hand two I would have most likely just called villains min raise preflop, especially if villain is loose as you said he was. No reason to bloat the pot OOP again here. As played, if you want to bet the flop, bet full pot as I think it gives you much more FE.