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 cost of repairing a cracked glass can range between $107 and $317. A technician will need to measure the dimensions of the glass and order a new one unless it is a stock size carried by a manufacturer. If your skylight is over 10 years old, chances are that you will need to have an entire new skylight installed.