I met with the contractor today and got a good picture of how the bid fits with my wants. The next step, he took a piece of the siding to be tested for lead and asbestos. We found a name on it, insulbrick... a faux wood grain gray shingle, rather like very heavy asphalt roof tiles. He'd never seen it before, but thinks it probably doesn't have asbestos in it... that would be nice.
He'll meet with the city inspector and see how the back room foundation holds up. We compromised on asking for a single window dormer in the loft. He thinks the inspector may require a new electrical panel.
Once we get the go ahead I will schedule a party and have friends come deal with the back room, carport and chimney demolition. I'll donate a portion of what I save to my church's elevator fund and put the rest to other options on the house. I was glad the contractor was willing.
Knock on wood, demolition day could be in two weeks.