Lots of people say they're going to do it. I've never personally known anyone who actually bothered, though.
Yes, it's probably a lot of work. The easiest way I can see it happening is if someone has a place to store cars in Atlanta or wherever they are coming from. Guy here pays for car and has it dropped off at the storage site. When the number of cars reaches a critical mass, then they get transported.
There's a lot of ways it is a PITA, but it has the advantage of the buyer and seller making their deal directly, instead of the transporter taking "orders" or just guessing at what kind of cars to bring up, fronting his own money on that gamble.
I'd wait 6-12 months for a clean shell. It's easily worth $500 to me to transport, since it'd cost more than that for me to tow myself, vs. it costing WAY more than that for a clean car up here. Not everybody can luck out like one of my friends did, who bought a rust free 240Z (it has rust coloring everywhere, but the floors are original and solid, which is mint for a 240Z) after the guy who shipped it here from the SW had to dump it at a huge loss after his wife found out when the transporter dropped it off in his driveway.