The pies come well-wrapped with eating recommendations and an easy-to-use box cover to keep them fresh. They come with eating directions which is basically to leave them at room temperature, how to warm them up some in the oven when eating, do not refrigerate, and to eat them within the first 3 days. It usually doesn't take us that long. Which is to say they're fantastic. Obviously I can't know what these taste like right out of the oven. But they taste quite fresh and outstanding for those first few days. The dark-chocolate cherry ganache (warmed up a tiny bit) and blueberry I had were just outstandingly, delectably delicious. So I'd guess whatever freshness is lost in transit is negligible. They tell you what day it will arrive fresh. And it does.
That said, the pies aren't exactly cheap, for a pie once you add in shipping. But I'd still much rather order and ship one than make one and mail it myself. So for a DBR bet they're really fun and fully worth it win or lose IMO. I started off trying to bet beer which was a royal pain because it's basically illegal to ship, and even trying to do so online was more trouble than it was worth. These pies have been just right.
Go win one and eat it with your sporks.