It's Not Flat, stop trying new math on the problem
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Common Core math.
http://www.kappit.com/img/pics/201509_1635_afece_sm.jpg
Knowing the rough size of the roof, this isn't actually that far off.
You have to find the area of each shape individually because of the slope. The measurements are actual, just drawn on an image that is "in scale" so it looks the same as if you were viewing the roof from a bird's eye view. I didn't measure eave to ridge, except for along the hips and valleys (which isn't helpful). A friend suggested that Wolframalpha can do this for me, and I may start using that program to save time.
So how far off was my 1001sqft guestimate?
Well, I'd say over 900 sq/ft off, but I'm not sure I'm comfortable with the way I came to my answer. I'm going to see what wolframalpha says.
I'm laying in bed with my iPad after a few glasses of scotch. Math is a bit harder, but inventing things is easier... Got any niche problems that need solving?
So what was the roof pitch? Was it consistent throughout? That will make things easier.
The triangles you measured out are simple trig, but the other shapes are a bit tougher...