Toronto winters on average seem to last 6 months while for Montreal it is 7 months. Also, Montreal gets more snow than Toronto on average. Montreal's average snowfall for a winter season is 85 inches and for Toronto it is 52 inches so on average Montreal gets almost 3 feet more snow than Toronto every winter season. Montreal seems to be at its best in summer, late spring, and early fall. I just don't see how it would be nearly as great in winter.
For a broken window (or leaking seal in multi-pane unit), for a standard roughly 2x3 foot window, can run from low of about $75-125 for single pane to more like $200-300 range for triple pane, depending on construction and any special ultraviolet or heat reflective coatings.
1 A front windshield typically costs $10-$150 to repair a chip or crack, and $100-$400 for a replacement, although it can cost $500-$1,500 for a rare windshield. Replacing a small, triangular side window (also called a quarter glass window or, if it moves, a vent glass window) can cost $100-$500 or more, depending on the year, make and model of vehicle, as well as the difficulty of installation.