the roof doesn`t sound way high,you have about 1500sq.ft of roof,you are removing 4 layers,1 of which is cedar shingles which is a nasty cleanup,and a lot of work cleaning the firring strips/purlins before you can install all new plywood,the flashing at the perimeter of both dormers needs to be replaced,as well as any chimney flashings,etc.--as far as the foundation,it would probably be easier to get someone to jack up the house in those ares,and put a foundation underneath-the other way you have to lift the entire house to put continuos joists under the house from the new front and rear walls(big job),you should look at sprayed foam insulation for the rafter spaces on the cathedral areas of the house(sloped ceilings)because the R-value is much greater per " than fiberglass,and the fiberglass is nowhere near enough.fiberglass (6"=R-19,foam1"=R7),ALTHOUGH YOU MUST BE SURE TO MAINTAIN AN AIRSPACE BETWEEN THE ROOF SHEATHING AND THE TOP OF THE INSULATION FOR PROPER AIR FLOW,these things can drive you mad,just take it one step at a time,and be sure to pick the right contractors for the job,---please post pictures of your house/roof so we can give you better information