Great comments!
As a buyer, if I don't need to satisfy a mortgage lender (cash purchase), then maybe I don't worry about homeowner's insurance. It's my decision.
As a seller, if I have an older house, it only makes sense for me to bring the house up to make it "sellable". In most cases, it makes the house more sellable with a new roof.
We recently bought a 30 year old house in Spanish Springs, but did so only because the previous owner knew that any buyer would have trouble getting a mortgage unless the roof was replaced.
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