Gil takes the bag, and then hills out his hand for the list if things, assuming it's ready to go. He sure has everything planned so far.

Five is lucky in the sense that Gilbert doesn't see him as "just a kid" because he knows appearances are deceiving and tell one absolutely nothing.

"I'll trust you on it."

Meaning, if he finds out there isn't enough money for all the supplies, or the other stiffs him on pay-out...well, he's not going to assist the next time.

"Are there any items on there I'm going to have to go out of my way for? Or should they all be easily picked up in town?"

It never hurts to cover his bases.