1. He wants to fix her skirt, but is afraid of her waking up in the process of him doing so. Then maybe just fix it from a position you can't look up her skirt instead of moving from such position to a one where you can look up her skirt WITHOUT EVEN TOUCHING IT.
2. What, I, a guy who spent most of the time playing games on pc - unathletic (zero fat tho), wouldn't be scared of jumping from that rooftop, on top of that he can just climb down the ladder and jump from the ladder down. What a loser. What an unintelligent individual that guy is.