I am getting ready to re-roof my hanger and shop / office building. I simply used my 100 ft tape to measure the actual roof: Got up on the roof, hooked the tape over one edge, went up over the peak, and measured down to the opposite edge. Measured the length of the roof sections and did the same in all directions on both the main hanger roof and the section that covers my shop and office. Same with the porches.
Multiplied it all out and added up the results. This gives a very accurate figure. It also allows the underlayment, starter courses, ridge shingles and metal valley flashings to be accurately measured and estimated.
Since I will have to pay for delivery over a mountain road from the dealer about 30 miles away, I don't want to have to do it again, and also want to make certain my roofer has everything he needs.
Interesting is that another roofer (not the one I am going to use) gave me a quote based on using 20% more material than will actually be necessary. When I questioned his figures, he said something along the line of "It's difficult to accurately know the actual size." He had simply measured the building walls and guessed at the overhang and slope, then added whatever he thought he could get by with. Of course he was going to charge me for all the extra in his fixed price quote.
We will use 5000 square feet of shingles (150 bundles) for this project, and if previous experience is correct, we should only have between 3 & 5 bundles left over.