Not to be ignorant, but this is where high school geometry class
is supposed to click in. Break the roof into easy to figure "pieces"
add them all together, add 10% for waste.
I have found it pays to use the heaviest (measured by year) overlay
shingle, Ice and Water Shield, 30# felt, starter strip, and real double
dipped galvanized (not zinc plated) nails. Also, do not use the flimsy
rubber stack flashings, instead get a tinbender to make up copper
stack flashings that you can curl into the stack. For valleys, if you
can't afford copper, next best thing is painted aluminum coil stock
(painted both sides) as wide as can be had, and put down first on the
bare roof deck, entirely covered over with felt. "The roof shingle should
only be there to make the roof pretty, while everything underneath should
be there to keep the water out" is a good way to build a roof that will
stand the test of time. There should be How-To books at the big box
store, or at the bookstore that will help you out.
Good luck
Uncle Bob