"I'm not sure hiking is his thing, as he frequently offers to pay for pizza on the trail if someone can get it delivered to a nearby fire road. "
Okay, my turn. True story. I was on a short backpacking trip with 2 female friends. They were fairly slow hikers, so I'd hike ahead a couple of miles, then turn around and hike back to where they were, then turn around and hike back ahead, etc. (I once had the hiking nickname of Double Back).
We were hiking the Laurel Highlands Trail in PA, where you use wooden lean-tos (Adirondack-style shelters) to crash in for the night. I made a few jokes about having pizza delivered to our lean-to as we headed out for the day. Unbeknownst to my hiking companions, I had actually ordered a pizza the night before, put it in the fridge and then put the pizza in a couple of ziploc bags, and folded up the pizza box and put that in my pack. I had also put three organic dark beers in a cuben stuff sack with ice and put that in my pack.
I got to the shelter well before they did, took the pizza out of the ziplocs and put the slices back into the original box. I then opened the stuff sack with the beer, which still had ice in it (it had been a nice, cool day) and folded down the sides so that the beers were nestled into their cuben ice bucket.
When the women arrived I asked them if they had seen the delivery guy since he had just left. Their pshaw-ing and laughter turned to astonishment when they saw the pizza and beer! And boy was that beer good. Pizza was pretty darned good too after we warmed it over a fire.
Fun trip. And yes, I carried the empties out.
And no, this has nothing to do with floorless tents, sorry. But I do own two, and I like them, but only for winter.