If anyone needs a roof fixed or a new roof altogether, I can get really good deals..my guy does high volume so they can afford to give 130 mph architecture shingles at the same cost of 3 tab 60 mph shingles. 

A new upgraded arch shingle roof last year.

I'm a broker in Oregon and the two companies where I have "hung my shingle," not only provide great training and mentoring, but I'm not giving up even close to half my commission.

I would also be demanding they shingle the roof as opposed to simply repairing the damage.

Maybe you want to keep doing the same project management for a log time or hang a shingle on a firm of your own.

If it's asbestos siding most areas do not require you to remove it, only shingles that are damaged, they make composite shingles today that match so you can make any repairs.

That's probably not too far off right now. 30 year shingles at Lowes before tax are running about $110/sq, add in your felt, nails, sealant, tear off/lay down labor and I'm not shocked by your quote.

If yours does, at a minimum you'd need a Salesperson's license and would need to "hang your shingle" in the shop of a licensed agent and be covered by their E&O insurance as they are basically responsible for your actions while managing property.

original electric  maybe 60 to 100 amp , not enough for today , old steam boiler  ,  galvanized plumbing ,  terra cotta sewer pipe clogged with roots , 3 layers of shingles on a 12/12 pitch roof ,  termites , Lead paint , no fire escapes ,  the list goes on .     

There are about twenty other random shingles that have fallen off in on other parts of the house.