In my opinion, you should fly to MD and either a) drive it home yourself if it seems like the 280Z be roadworthy enough, or b) when you get to MD, rent a Uhaul truck and car trailer and tow it home yourself. In either case, take a route home through the southern states to reduce your exposure to winter weather as you head towards home.
I'm sorry to hear your good friend isn’t well, and I hope he recovers. But it’s great that at some point, you’ll be the next person to care for that 280Z. Welcome to club!