In 2003 I bought a house with nearly identical situation. The roof had a hole the size of a football in it. I crawled the attic and realized the damage wasn't too bad. So we paid 800 out of pocket before my bank and insurer would even entertain the note. As is, the place had great location, good bones, just an old house that needed work.Looks like I might not be able to buy the home I was hoping to. Since we are financing and I disclosed that the roof leaks, no company will give us homeowner's insurance, which is required for the mortgage. The house is being sold as-is so nothing I can do. I think the realtor assumed I would lie about the state of the roof to our potential insurer.
I prayed that God would put up obstacles for us if it isn't His will for us to move. I'll take this as an answer unless a simple solution comes up.
Now I'm not sure if I should continue saving or looking for a home. I really wanted a home for safety (as we live in a diverse area in a major metropolitan area) and as a hedge against inflation.
That 800 was good to me. We had instant equity once the deal closed on a habitable home (all the other bidders have the same problem, and it kept the sale price under control). Sold a few years later for a nice profit before 2008.
That "obstacle" may have been a gift, if you can swing a deal on it.