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Underlayment is required by building code, so any roof installed without it is technically against code. The underlayment acts as the second layer of defense against water, so installing a roof without underlayment means a much higher risk of roof leaks. You’ll have the best chance of avoiding roof leaks if you install drip edge flashing covered by underlayment, and then install your roofing material over that.

Re-roofing is the process of placing a layer of shingles over top of existing shingles, rather than pulling out those shingles and replacing them. Compared to a full roof replacement, re-roofing typically costs less and requires less labor and time. It's not an option for everyone, though. You may need a full roof replacement if your roof already has more than one layer of shingles. A full replacement may also be necessary if your roof has extensive damage.

There are two main types of roofing shingles: 3-tab and architectural. Architectural shingles cost more than 3-tab but offer a more unique look and can last longer. However, 3-tab shingles are lightweight and affordable, and many people use them for both patching roofs and installing new roofs. Ultimately, the best type for you depends on your budget and your home’s aesthetic.

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.