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Yes, because it prevents water damage, deters pests from accessing the roof decking, protects the roof from wind damage, and lengthens the roof's life. Plus, building codes require it. 

EPDM roofs have a few common problems, most of which can be resolved with regular maintenance. This type of roofing is laid down in sheets with seams, which can be a starting point for leaks. Proper installation and roof sealing can often avoid seam issues. 

The material is also susceptible to tears and punctures from falling branches or other sharp objects. There are black and white versions of EPDM, and the black version is more prone to fade and succumb to UV damage. Regular roof inspections can protect the costs of rubber roof installation and extend the life of your roof.

Stripping existing shingles and installing a new shingle roof takes a professional one to two days, and sometimes up to three days for larger roofs. Additional safety measures necessary for steep roofs can extend the timeframe even further, as do added measures, like replacing roof decking or reinforcing your roof structure to support heavier materials like slate or clay.

Your chimney needs a structurally sound chimney cap, protective lining, damper, chimney flashing, and brick and mortar to prevent water from goind down your chimney. A pro can help you identify where the issue is so that you can stop water from coming down the smoke shaft, through your damper, and into your home.