Ah, the United States Postal Service.
On the one hand, our local post office is uncommonly friendly. Apparently my mother sends so many packages to my sister (at the Air Force Academy) and now my brother (Kuwait) that one of the clerks recognized my maiden name and described my mother and younger sister in detail to me.
And when I went to send these cupcakes last Tuesday, the lady who was ringing up the packages cheerfully told me that I was sending cupcakes ALL WRONG and that I needed the long mailing box and not the tall flat rate box. That resulted in me waiting until Wednesday to send them, but it also meant the cupcakes would get less jostled in the mail, so, worth it.
On the other hand, even when they ask if there are baked goods or perishables inside, they aren't very gentle with it after it leaves the facility. Perhaps there is no perfect AND cheap way to send cupcakes, but this method worked well enough, and with a few tweaks next time, maybe my brother will actually get cupcakes that don't look smashed.
Now, I am no baker. When I make baked goods, my first priority is taste, not appearance. I even took that stance with my wedding cake, turning down bakers who made gorgeous cakes that tasted like cardboard until I found my dream cake (and it tasted AMAZING). So when I was sending cupcakes, my first priority was freshness, and appearance took a backseat.