i've driven to florida the entire way from dover in one go twice to meet family, i don't think it'll be too much of a problem. but that was with dry roads. i know it snows a lot up there, but experience will come and i'll be just fine.
Mostly interested in upslope, bigger coastals usually miss the area i'm interested in, but i can chase anyway. I buy bulk foods a lot, rice and beans, that sort of stuff. Shouldn't have too much of a problem with groceries. Cost of living seems lower there than NY or NH/MA.