It is never a good conversation when a contractor says "it could be an easy $20,000-$30,000". Our house is fucked.
I had another contractor, who specializes in structural repairs, out to look at our bowing wall/sagging roof. This guy was the first to say "oh, you'd be better off doing an addition to add a second level". I try and explain to them that:
a) I don't have $100,000+ to do the addition;
b) even if I did, the neighborhood won't support it;
c) I'm not planning on staying in this house more than another 5 years.
I'm sure if b were a yes, and I could get the bank to help me swing a, then I might consider changing my mind on c.
This guy was honest about it. He said EXACTLY what I expected: the entire roof has to come off the house and be reframed.
we also decided we're gonna get bro tats of "die hard" on our asses. ha.