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The short answer is, yes, cedar shakes do last longer than asphalt shingles. But the long answer is, it depends on maintenance. Asphalt shingles last about 20 years, while cedar shingles typically last about 30 years with proper maintenance. If they are very well maintained and installed in an area with a mild, drier climate, they can last up to 50 years.

You’re going to need a permit for nearly every roof-raising project. This is a very important step, as the work you’re doing has serious safety considerations. Professionals are the ones to handle this type of work—including sourcing the permits—as they have the expertise required to perform the work safely. Insurance and warranty are usually voided if you do this work without a permit, and you may even be required to halt construction and tear it down as a penalty for working without a building permit.

Properly installed chimney flashing can last anywhere from 15 to 50 years. However, flashing generally only needs to be replaced when it is damaged, corroded, or no longer creates a watertight seal. Several factors influence its longevity, including the material type, quality of installation, and local climate. For example, copper flashing tends to last longer than galvanized steel. Large storms and extreme weather can also damage flashing, potentially requiring earlier replacement. To ensure its longevity, it is recommended to have your chimney and roof inspected annually. A professional can assess the flashing's condition and recommend any necessary repairs.

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.