Ward -
Sounds like a GREAT idea to me. I'm about to embark on a similar venture, myself. The wife and I are Wintering at a Cobra buddie's condo near Daytona Beach. I hauled my '65 Mustang convertible down here in an enclosed trailer - having a blast driving around with the top down.
We are planning to drive down to the Keys during Bike Week, and were going to take the SUV. However, after thinking about it, I decided the trip would be a much greater adventure in the Mustang convertible. Don't really relish the idea of leaving it out overnight in hotel parking lots, but, maybe the cover will help disguise it a little.
I would go with your plan the way you suggested - drive it around Florida and enjoy the sunshine, then ship it back home. A cross-country drive with the little woman in the Cobra might be a little bit of a tough sell.
enjoy!
Jeff