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Homeowners insurance typically covers roof repairs or replacement if the damage is caused by a sudden, accidental event or a covered peril, such as a storm, wind, hail, fire, or a falling tree. However, insurance will not cover repairs or replacement for issues stemming from a lack of maintenance, normal wear and tear, or a roof that is simply old and at the end of its lifespan. If a leak or damage occurs due to neglect, you will likely have to pay for repairs out of pocket.

A roof replacement will usually include removal of your old roof, shingle replacement, and a new roof underlayment, but it may only include adding new shingles if you’re layering new shingles over the old shingles. If you have signs of roof leaks or your roofer finds water damage to the roof decking underneath your old roof, it can also include replacement of the OSB or plywood decking that lays over your rafters and supports the roofing material above.

Fall is widely considered the best time of year to replace a roof. The moderate temperatures are ideal for roofing crews to work and for new shingles to seal properly. Additionally, autumn weather is often drier, reducing the risk of weather-related delays compared to the rainier spring season.

While spring is also a viable option, the higher chance of rainfall can slow down the project. The main drawback to a fall installation is that it's the peak season for roofers, which can lead to higher prices and scheduling challenges.

To potentially save money, you could consider scheduling your roof replacement during the summer or winter off-seasons. However, both seasons have significant disadvantages. Extreme summer heat can make shingles too soft to handle, while winter's cold, snow, and ice can create dangerous working conditions and prevent shingles from sealing correctly, as they typically require temperatures above 40-45°F.

If your roof has a vapor barrier, you will need approximately one square foot of roof vent for every 300 square feet of ceiling space. If there is no vapor barrier, the roof should have one square foot of roof vent for every 150 square feet of ceiling space. If you are not comfortable making this determination, a local roofing professional can help.