You don't state your general ages.
If you qualify for membership in AARP then you should really give all some serious considerations.
It is frigid cold here for about 10 weeks. You have to shovel the snow. Or work a snowthrower. Pay to have driveway plowed or do yourself.
Ice is a big issue. Whether walking or driving.
Myself - I fall down at least once per winter. Ice under snow. Walking in a dark area. Or just not paying very very close attention to ground.
Every snow storm there is at least one car accident in my town. Sometimes more. Usually when snow storm begins before all plows/salt/sand is put down. People either going too fast or tires on cars are worn. AWD or 4WD does little help on ice.
Depending on where your choose to live - shopping can be a real chore.
Home maintenance can cost much more here. Wood homes with asphalt shingles. Seems to be either painting the home or replacing the roof.
Depending on age of home heating costs can be quite high.
Social activities can be limited. Of course, there are church activities, civic organizations, and volunteer activities to keep busy.
Do you have family here?
Can you afford one home here and one in Florida?
If I had been living in Florida for many years - I would not pack up and leave for cold climates. Just because I had some romantic views of New England.
Possibly do a winter rental for one winter. There are many homes in the Lakes Region that have reasonable and seasonal rents from September to May. Try it out first.
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