Welcome to the RTA Forum!
It sounds like you've got an excellent plan in front of you, and we wish you the best in finding a companion.
I will offer you just one little bit of a warning. If you are hoping a stock Mustang convertable will be a true muscle car, you may be disappointed. The rental versions are pretty stripped down, with a V-6, base suspension, and the like. It should still make for a nice trip, but if you really want a muscle car, you might want to spend the extra money for a car in a specialty collection (like the Hertz Fun Collection). It might cost a pretty penny, but if you can afford it, it might be more along the lines of what you are looking for.