Quick Answer: A complete annual Calgary roof maintenance checklist runs on a twice-yearly cadence: spring (April/May) for winter damage and pre-summer prep, fall (September/October) for winterizing. Add event-driven checks within 48 hours of any hailstorm and 2 weeks of any wind event over 90 km/h. Core tasks include eavestrough cleaning, flashing inspection, vent boot check, attic moisture inspection, ventilation balance verification, and documentation photos. Most Calgary h