This has been a fascinating thread to read, and, yes----I have felt so many emotions as have been expressed on here more than once!
When I took off for Florida a couple of years ago after I retired from many, many years of teaching, hauling my little trailer behind my truck, all by myself, I have to admit I came so close to not leaving this house despite the realization that I would simply die having to face another extremely cold and snowy winter carting firewood into the house each night, spending the long, dark, freezing nights all alone, (no neighbors here, either) worrying about the pipes freezing, the power going off, and on and on. My son lives in FL, so I knew I had a spot to park my trailer, and I have a house in the Orlando area that belonged to my father. BUT----when behind the wheel, on the open roads for that first time, with my daughter accompanying me for the first 20 miles through the little towns I was afraid to haul through, I pulled into a McDonald's parking lot wrong to pee and get a cup of coffee and drop her off in the other car. I couldn't back up, I thought, so I just started crying and saying I was going home. I can't haul, I can't pull into a parking lot without having to back up, I can't relax enough to not cry----I was going home. I went into the place, and when I came out, Joe, Mandy's guy, had turned me around just like a piece of cake! I had no excuse. I turned out towards the road, almost in the HOME direction, then changed my mind, and headed south! (I 'eased' onto the road!) I cried until I got to the main highway south about a hundred miles later! "Why am I doing this?" "Can I make it all the way?" "Will I get stuck on a dead end street?" "Can I find a gas station when I need it?" Can I get out of that station! And on and on with needless worries. That first time I met an old college friend of mine in Syracuse who traveled the remaining miles with me for the rest of the way, or I doubt I would have persevered. But I have done the 1500 miles alone now three times, and each time it gets a bit less terrifying and almost fun!
As far as going to the FL GTG, if you won't be there for the winter, that would be a much too far drive for just a week, I would think. However, if you find that between now and then you find a way to leave New England for this winter, with enough funds to exist in a cheap camground somewhere, as was my original plan until my son bought his property, you could brave the elements and face down your fears by taking the trip just a "little trip" a day, as many told me to regard one long trip! It works, for me! I now travel about 200 miles per day, and find a safe place to stop for the night, either at a Flying J Truck stop, for free, or at a campgound when I get south enough for them to be open. When I know I have a couple hundred miles to go each day, it seems less daunting.
Hang in there, and know you are most definitely not alone!