You'll have to tell us the story sometime! I don't buy new either.
Roofing
looks hard. I once did a lot of work to a house built in the 1880s (like my car work, a hack
) and it was interesting. Not only were the exterior framing timbers all different dimensions but nothing was plumb or square. The windows appeared to be built on site and doubled as the opening framing. The trim peaks on the front windows looked like this: _/\_ and each piece of wood was cut multiple angles in every direction to shed water! With a lip in the back to boot. Ditto for the flat porch roof (Victorian). I have a ton of respect for those old craftsmen. When I need a hand I'll give you a call
Pete