You might want to chat with
@FLBiker, who has moved from Florida to Nova Scotia, for a first hand view of the acclimatization process.
I've lived in brutal winter Canada all my life, so maybe my sensibilities are different than yours, but it's really not that bad. Winter doesn't hit all at once, so you have time to adjust and prepare.
Electric heat in a house is easy - just turn the dial. No real maintenance required, other than an occasional vacuuming to keep the units dust-free. I don't know much about wood stoves, except make sure it's new enough that it's safe, have a sufficient fire-proof surround (tiles, etc) and the chimney is cleaned annually. Get a professional for this - not worth risking a fire to save a few bucks.
Make sure the roof and gutters are sound and in good shape for snow load and the spring melt. Clean out the latter each fall after the trees are bare. Extend the downspout well away from the house to avoid seepage into the basement.
For general weatherproofing, the utility company probably provides an assessment of your house for a fee, or possibly even free of charge. They will recommend upgrades/repairs to keep your house energy efficient. Some provide grants for the work. Things like insulation for the basement, attic and walls, windows/doors and weather stripping can save a lot in the long term. Basement insulation will give you more bang for the buck than upgrading the attic, if you have to choose an order. Make sure water pipes are wrapped in foam insulation in the basement up to where they meet the exterior walls, to keep them from freezing.
Snow shovels, both scoop and push types are important, plus sand or ice melt for slippery sidewalks. A corn broom is good for a light dusting of snow, or a leaf blower for bigger areas. An ice chopper wouldn't hurt either. If you have a driveway to maintain yourself, a snow blower, possibly.
Also, a car snow brush, although a broom is faster/easier, in my opinion. (Lock de-icer too - keep it in the house, not the car!) Also, an emergency kit for the car - blanket, candles, etc. I like Michelin snow tires, but I'm sure other brands are fine too. Talk to the tire shop about prices and what they recommend. If you get lots of icy roads, studded tires may be the thing, if allowed there. Get your car winterized around Oct/Nov. They'll check all the fluids and replace for low temps if needed. Also make sure the battery is up to the job of starting in the cold. A block heater to plug in is likely necessary there, and an interior car warmer will keep the windows clear without having to scrape.
For clothing, layers are best. Thermal underwear, then your regular clothes, probably 3 different weights of coats, light for early fall and spring, then medium weight (3 in one's are good), then a parka with hood for dead of winter. Scarf, mitts/gloves, hats, boots. Ice grips for the boots.
I think those are the basics. Ask neighbours/co-workers for advice/help for whatever you don't know. It will be a learning process for sure.