If you keep an eye on the weather, plan your passages and don't get impatient, should be no problem. You will need heat, however. Weather will be cold and getting colder with each passing day. Still, there are short sessions of relatively mild weather even in the dead of winter. Hey, you are Canadian, you are experts on Winter. Haven't spent a fall north of Norfolk. Did
live aboard there for one winter. Winter didn't really hit till after
Christmas. Weather in the 50-60 range prevailed though did have one short lived cold snap. After
Christmas it got a bit chilly. Regularly froze at night and daytime temps in 40s with very occasional snow and subfreezing Wx. Began warming up in March. Expect you'd have to get to South Carolina to get out of freezing temps, Northern
Florida for 50-60 degrees and southern Fla before you can break out the swim suits. We made a trip from Norfolk to Maine in March. Left 70s in VA to 50's in
NYC to low 30s and snow in Maine. Plot that in reverse and you'll probably find what you can expect in November/December going south.
The boat will be a challenge with two large dogs. But what's life without challenges. When we were young and foolish, we lived in a VW Bus with a 60# Lab and 7 puppies while building our Westsail Kit. Boat seemed like a mansion after the bus. You'll have to learn to adapt to the limits but you'll do it if you want to.
I've got a
diesel Newport Heater in my
current boat. Keeps 35' boat very toasty though needs a fan running to distribute the heat. Installed a separate 12 gallon tank for the heater
fuel.
Good Luck, it's a great adventure that even my non sailing loving wife looks back on fondly.
Aloha
Peter O.