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About the roof. A roof inspection is a nice start. But only a start. It's nothing if it's not insurable. So the next step is contacting the insurance agent. Be clear on how much longer he/she will be able to insure it. There's a whole age thing, however good or bad it looks now. Then consider if the insurance company's rule of thumb for how long they can insure your roof works for you. Where I am and in talking with friends I discovered the 30 year old roof would be past insurability. A few years past. Our roofs were great but there is a rule of thumb they won't go past. That's the thing about insurance. They are careful. (That said, another friend says his agent will go longer.)
We weren't going for a loan when we discovered this. Actually, just chatting with our insurance agent.
You might consider, since asking if free, ask your insurance agent you would use what is rule of thumb is. If it's good for you, pay for the guy to go up on the roof and do his inspection.
I am using the same agent that sold me my place in 1997 to sell it again in 2019 because of his attention to detail.
A great attribute of a realtor will be to guide you through what needs to be done minimally to get a sale.
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