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Roof underlayment usually lasts as long as the roofing material that covers it, as it’s not directly exposed to the elements. In most cases, roofing companies will replace the underlayment each time they install a new roof. In some cases, particularly with slate, clay, or certain metal roofs that can last 50 to 100 years, your underlayment may require replacement within that timeframe, especially if you start to notice roof leaks.

Most roof leaks occur where shingles meet or where there are sealants or seams in the materials. This is common around skylights and at any point there is a break in the roof such as corners and edges. Roofing materials are incredibly strong and resistant when overlapping, but any change in that can cause gaps where water can enter.

If the bay window extends beyond your existing roofline, you must add a roof or a small “skirt” to divert storm water and prevent water damage. The window roof can match your existing house roof, or be finished with copper or other decorative materials. Most bay windows have a roof with complete flashing regardless of their placement to prevent leaks into the home.

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.