Well, nice surprise... my contractor buddy was able to shave $1000 off the price of roofing materials by letting me use his account. (And paying cash)! It's who you know in this world... I ended up paying a crew to install the shingles. since I did the tear off and will handle the cleanup, they were able to do it very inexpensively and quickly.
Anyway, Here's some pic's of the tear off, and one of the new roof, where the addition transitions to the existing structure.
Pro-tip: If you do a roof tear-off, here's how to make it easier.
-Spend the money on a dump bin. Handling this stuff twice to save $250 isn't worth it. Beleive me, we did this on this project and it sucks.
-If you insist on using your pickup/trailer to haul the stuff, put the tarpaper down in the truck first. When you have 4" or less of debris in the truck, it all will just slide out of the back of the truck, saving some time.
-Get a cheap harbor freight square nose shovel. grind two v notches, 1/4" deep, spaced at 5.5". This lets you pull two rows of nails (and therefore flights of shingles) at the same time. The shingles also come up more or less whole, with the nails still in the shingle, for easier handling.