You actually have a 1650 SF roof that I would order 20 SQ (2000 sf) of shingles for. Price depends on what you can get materials for. It has been a while since I have installed a shingle roof and a roofer friend of mine told me prices have soared since the $4 a gal gas prices. Neither my friend or I are familiar with retail prices. Contractors can get pretty good breaks from supply houses. 'Jim from Canada' may be able to help here since he recently had a roof installed.
Anyways, if you take a roll of Ice & Water Shield or WeatherLock and cut it lengthways down the middle (3' wide), you can install 18" on all eave areas and have enough left for some vents. If you want to do the ridge caps also, you will need a second roll. I will figure one roll. I will figure two layers of 15# felt over the entire roof surface. They are put on with a 50% overlap to get 2 layers. This is a requirement from most shingle warranties. You can use 30# if you want, but the warranties still require two layers. You would double the price of roof felt. 15# = 4 SQ, 30# = 2 SQ
Also, roof-top delivery could be available for anywheres from free to $150. Believe me, it is so worth it. They show up and use a lift or conveyor. The free guys might want you to load the roof while they hand them off to you.
These are just approximate prices. I think they are close to what you would pay. After making the jpg below, I think you may need one more roll of felt to complete the job.
Again, this is just how I would prepare the order. No guarantee that you won't need a trip to the store. New vent caps and replacement sheathing is not included in my figures.
JD