Intro
You will order roofing and underlayment by the "square" -- that is, 100 square feet. To estimate your needs, calculate the total square footage of your roof. For the most accurate measurement, you could actually go on the roof and measure each section, but that is often difficult and time-consuming.
More commonly, square footage is estimated by measuring from the ground and then making some simple calculations. (However, you may need to climb up on the roof to measure dormers or other protrusions.)
Once you have calculated your roof area, do not subtract for small obstructions such as chimneys or skylights. If you have dormers, climb onto the roof and measure them or make a rough estimate. Add up all the roofing sections; add 10 percent for waste.
Arranging for delivery
It's not a good idea to leave bundles of shingles sitting on the roof for days, so delay delivery until you are ready to roof. Watch the weather reports; you can't roof when it is raining. If the roofing will be delivered onto the roof, have it delivered after you have installed the flashings and underlayment.
If it will be delivered to your yard or driveway, have it arrive sooner. If you have to move bundles around, do so safely.