We are in Mass, about 20 mi. north of Boston. We left Thanksgiving night at 10:00 PM, and arrived in Orlando @ 10:30 PM the next night. Not bad time, we thought, considering we travelled w/ a 4 yr old & 2 yr old!
There was a rather large snow storm, if you remember the day before Thanksgiving, which made us nervous about road conditions, same as you. We had 2 weapons that eased the fear: the CB and the cell phone. The CB is great especially at night. The truckers never shut up-keeping you awake on the road, and they can tell you the road conditions usually through the whole state. We would get on the radio at each state line asking how the roads and speed traps looked. Usually, you get a few drivers checking in, and they know what they're talking about! They not only could tell you every pot hole, frost heave, and lane shift, but every "Statey" as far as the state line!
The cell phone, obviously, is the just in case we needed
AAA to pull us out of a ditch, safety item.
BTW we leave between 8-10 PM every time we drive (6 trips now) as it basically puts you south of DC if you really try for it. We made it into VA by 7 AM this year. Once you're south of DC, NO TRAFFIC at all! It's a beautiful thing! I have more details on timing, roads travelled etc, if you want.
Coming home, an ice storm hit the Carolinas and Virginia the night before we went through. The roads were untreated, but not iced over. The problem was the trees that had fallen into the road-they were not moved. We played dodge 'ems up to almost Richmond!
We did run into some iced over bridges, however, both coming and going. Just take note when you are coming to a bridge, adjust the cruise control down to about 50, and you'll be fine. The signs warning you that "bridges ice before roads" may be kind of a joke here, but down there they mean it. The road can be totally bare, and then all the sudden a nice frosty bridge sends you fishtailing across 2 lanes.
My opinion, go for it. The cost of gas & tolls round trip is about the cost of 1 airfare Manchester to Orlando. And we really encountered no trouble that couldn't be handled with a little New England winter driving know-how!