I didn't know how to title this thread, because there's really much
more wrong with the 1832 property than you could fit in a thread title.
But we still want the house.

I don't know the exact square footage, but there are ten (small) rooms,
so many different kinds of services (oil tanks, two of them, two water
heaters...on one water bill, various electrical "patchworks"). I want
to use the first floor, which is definitely the nicer one, as a primary
residence and continue to rent out the upper to the decent tenants now
there.

I know this is asking a lot, but could anyone give me even a ballpark
estimate for the following:

1) Cutting through clapboard and ancient planks to install a second,
upper stairway (so that the home may qualify for HUD tenant subsidy)?

2) Totally rewiring the home for two services (so that in mid-January,
tenants don't plug in space heaters, keep overloading the breakers, and
burn the house down)?

3) Tearing down ancient gypsumboard so that the high-ceilinged first
floor could be insulated?

4) Replacing 19th/early 20th century NON-WEIGHTED double hung sashes
with the cheapest alternative (about fifteen standard-size, @ 3' x 4'
(?) windows)?

5) Replacing the @ 3' chimney.

A real estate/home inspector knowledgeable of the home said he did an
"APOD" on the home, a former bed-and-breakfast, and that the cash flow
was so negative it almost went into the imaginary number system. But I
don't want to use the place as a bed-and-breakfast, and if I have a
positive cash flow of even $1 a year, that's fine, because I plan to
use the place as a primary residence.

Oh well, I suppose you'll make fun. I just need some non-mockery.