If the roof’s age is unclear, it might need replacing soon.Electrical systems can be tricky in older properties.

Many carriers have ceased offering new policies or will only accept properties in very nice condition with verifiable updates to the roof, electric, hvac, and plumbing.

Most recently, I worked with a client out here in Colorado that let their parade of homes house (from 25 years ago) in a gated community literally fall to pieces; mold between window panes, water infiltrating the kitchen due to lack of roof repair, patio pavers crumbling apart, downspout misplacements that caused water infiltration into the living room....just a mess. 

I would say look at the big ticket items, roof, foundation, electric, plumbing, HVAC and assess from there if anything needs to be done 

He eventually put a new roof on my building and did an excellent job! 

What would you have done if your price was too high and you didn't know your roof was keeping people from making an offer to begin with?

You are one failed AC/roof/6 month eviction from going bankrupt.

Charming Little 3/1 - We are remodeling all inside and out including new roofing, this is our first project out of state, it will be a BRRRR, hopefully first of many to come.

Do you have any recommendations for contractors for roofing or plumbing/hvac?

Sometimes a little incentive can make them leave peacefully.Raise the Roof (Rent, that is): If local laws allow, crank up the rent to make them consider greener pastures.