Hand 1: Yes, you definitely want to get all the money in with this hand. Check raising the flop isn't terrible with 7 players and an unconnected board, but I'd prefer to lead out. I wouldn't overbet on the turn without a read. I'd make it 3/4 pot - pot sized bet. If you're confident that he'll call a push, then by all means go for it.

Hand 2: Looks fine to me.

You just got coolered here. Don't let the results phase you; it's whether you made the correct decisions that counts. Best of luck to you with the OP.

By the way, why does PT show amount won as ($0,016.15)? It should be ($16.15)