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Metal roofs do not inherently leak more than shingle roofs; when properly installed, they are generally less likely to leak. Asphalt shingle roofs are more susceptible to leaks due to factors like wind uplift, damage from extreme weather, moss growth, and ice dams. Over time, asphalt shingles also lose their protective grit, which reduces their waterproofing capabilities. In contrast, metal is a more resilient material that stands up better to heavy precipitation and high winds. However, metal roofs can develop leaks if they are poorly installed, have improperly sealed fasteners, or experience issues from thermal expansion. For this reason, professional installation and regular maintenance are crucial to ensure a metal roof's longevity and superior protection against leaks.

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.

You can technically install a metal roof over asphalt shingles, but it isn’t a good idea. This is because you’re essentially creating a moisture barrier under the metal, which can easily—and often does—lead to significant mold damage. Removing an asphalt roof isn’t terribly expensive, and some roofing companies might cut you a serious labor and disposal discount if you add it to a new install.

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.