Sean,
Before the depression forced retirement on us, we frequently traveled in the real winter and/or a month each side.
First lesson: If your fiver is capable of being self contained, be provisioned and ready to do so at least for the first two days out. This is assuming you will make for warm as fast as you can. When they get snow in the south, the world comes to a halt. You may end up "camped" on I-95 when you can see an exit ramp.
Second lesson: If you plan to stay at any campgrounds, call them now and find out if they will even be open those dates. If they are planning to be open (see above), confirm the winter facilities and capabilities. Many shut off the water and sewer.
Third lesson: If you have to make a reservation, get a VERY clear understanding of the owner's reservation policy. If you end up weathered in for a day (or two), can you get a refund for the time you are not there? Many more than you might think say no.
From experience - 14 hours is a long time behind the wheel. I a passcar or very comfortable coach, maybe, but in a PU towing a heavy fiver and with two massive dogs in the cab.... I used to tow a keel sloop all over the east coast. Places that were a couple of hours by car became three hours with the trailer and a boat.
Driving tired is one of the fastest ways I know of to end up dead.
Matt