Of course he has everything ready. If it's one thing Five hates, it's wasting time, and it didn't take him long to figure out they're missing some essential items. This probably won't be the first trip, but it's enough for now.

He actually looks impressed that he uses the words 'I'll trust you' when he takes the money. That's not a phrase he hears too often. In this case though, what he gave him is more than enough. The list he places in his hand after the money even has it tabulated on the side, letting him know what it should cost in the market by his estimation, and his math should never be questioned. He couldn't make it any easier.

"Decent coffee might be a long shot, but I'll take whatever you can find." He's tired of drinking tea, nothing they have is strong enough. There isn't that much on the list, but the alcohol is probably going to be the priciest and the heaviest to cart around, so he doesn't want to overload him.

And since he's being so considerate and all, he actually asks: "Do you know where you're going?"