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Yes, chimney flashing is an important element in the complex system that is your roof. Chimneys (and anything else that goes through your roof) provide a great opportunity for water damage. Good flashing prevents a lot of potential damage. 

Rubber shingles last for around 30 years, on average, and some can last for and include warranties for up to 50 years. Rubber roof shingles are more expensive than asphalt shingles, but they can last up to twice as long, meaning they provide more value in the long run. Just keep in mind that rubber roofs often require more maintenance than asphalt shingle roofs, including routine cleaning to avoid mold growth. Ask the roofer who installed your roof for an estimate for routine cleaning, if necessary.

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.

There is a weight limit for walking on a roof, but it’s determined by your roof structure and not the roofing material, at least in the case of a metal roof. Consider that entire teams of roofers will be on top of your home during the installation, so the weight of a single person won’t compromise your roof. That isn’t the case for something like a tile roof, so a high weight limit is one benefit of a metal roof.