Whatever you decide and whenever you go, I pray for you to have a safe and enjoyable journey. I live in the northwest hills of South Carolina not far from the North Carolina state line. I often refer to my region as being on the "edge of winter." Being that we don't experience the true bitter cold winters like the Dakota's, Wyoming, etc. However, today it didn't get up to 40 degrees. Right now the temperature is in the 20's and I have a fire in the fireplace. There have been occasions where snow has drifted and buried my heat pump causing me to have to shovel the snow away so that the fans could work properly. It is rare, but it happens.
If I were younger, I might be tempted to make a similar trip.
My thoughts are...this time of year, from your location, would be to take a southern route to the Gulf coast and ride it eastward toward Florida. Even then, you could be in for some fairly cold rain. That all depends on your time, patience, and a contingency plan for layover stays waiting for good weather. Keep a good smartphone handy so you have internet access to this forum. That way, if you encounter difficulty, you could reach out to some of us who might be able to assist. Or...at least express sympathy/empathy for your predicament as (probably in my case) I attempt to explain why I can't help you out.
Regardless... it sounds like a great experience. If you launch the trip, start a "road trip" thread, provide daily updates and let us enjoy it with you.