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.
The base price for float glass, which is clear window glass, is about $12 per square foot in 2013, and the price increases with every feature you add. Tinting adds from $5 to $7 per square foot, tempering adds about $2. Double pane glass is priced separately. If you add the cost of the glazing compound and caulk, the cost to replace a 2-by-2-foot pane of glass would range from about $60 for a clear pane to about $100 for a tinted pane of tempered glass. Don't forget to allow money for paint if you have to make repairs to the frame.