Download the sweet app called Pitch Gauge for your smartphone. You can stand directly in front of a gable end of the roof and line up the "level line" on the app and it will give you pitch, or you can put up a ladder and set the phone on the roof for a more accurate pitch. I carry a telescoping ladder in my sales/personal truck for estimates, it was kind of expensive, but I love it. Then there is a calculator function that allows you to do length x width, put in cut level (it gives cut level samples) and it will give you the # of squares. I have done it the long way to double check this app several times and it is always very, very close. I still throw a ladder up to an easy area like the garage to peek at the gutters. I now use Pitch Gauge every time. It's still good to know the old fashioned way, too. Never know when technology will fail or you get a roof that it just won't work for.
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Chad A. Eneix, President, Water Dragon Inc. chad@waterdragoncleaning.com