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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.

A roof replacement can take anywhere from one to 14 days. For most homes, a full replacement that includes tearing off old materials takes about one to two days, though the average project can last up to 12 days. The exact timeline depends on several factors, including the roof's size and complexity, the type of roofing material, the crew size, and weather conditions. Certain materials take longer to install; for example, metal roofs can take seven to 14 days because the material is more difficult to work with than asphalt shingles, wood, or tile. A re-roofing project, where new shingles are installed over old ones, can take half the time or less. It's also important to factor in the time needed to obtain necessary permits. A professional roofing contractor will typically complete the job faster than a DIY approach.

You can only overlay a roof once. Any additional layers of shingles will add too much weight and may also violate building codes. Once your roof has had an overlay, you’ll need to have a full roof replacement, including a tear-off of all existing roofing materials, when it’s time for a new roof. 

A roof pitch that’s too shallow won’t shed runoff as quickly, so you have an increased risk of water intrusion through the seams between your roofing materials. In colder climates, snow and ice will accumulate more easily on your roof, which can add enough weight to cause roof collapse and structural damage to your home.