Live on the hard in Montreal BBBBBRRRRRR
We lived aboard just east of Toronto, on Lake Ontario for 8 years. One year we hauled our boat out because we were planning to travel for a few months and when that didn't work out we were stuck on the hard. It was REALLY MISERABLE. People don't understand how even cold water has an insulating effect. At -20 C it was just unbearbale in the cabin even with all our heaters blasting away and insulation on the deck. Comparable to that -20C in the water isn't pleasant but it's warm inside.
And don't forget that you'll have to be up and down that ladder for every call of nature, to haul jerry cans of water on deck (You can't fill the water tanks because they will freeze) not to mention groceries, equipment and all the other regular necessities. And you can't use your drains unless you put hoses from your through hulls and jerry cans under them, but at -20 C they'll freeze too....
And Montreal gets way worse winters than where we lived.
Naw... there is a reason that boats are made to float in the water.