This is the driver for the tone of this tread. 

You tried getting a roofing job from Bob Prisco aka Bob Stevens, or you tried getting a roofing job from Elliott Taylor?

a property that was attached but the next door property had a door to the roof of it with a deck. 

If no, are there photos of each unit and all closets, the basement, the roof, the exterior, and all mechanicals?

It also sets a positive tone and builds trust with new tenants, showing them that their living environment is taken seriously and maintained with care.

Flooring, Drywall, refinish basement, roof, gutters, tuck point around house, and one full bathroom gut all had to be completed. 

The tone of his email implied he had been unable to reach my PM after "several attempts."

Basements (if they have them), roof, attic, crawlspace, exterior, and all mechanicals are where all the unseen costs are not in the kitchen, bathroom, etc.

You asked about buying older properties and the biggest issues I have found is that roofs need to be replaced, HVAC needs servicing/replaced, and sometimes there are foundational issues (not super common). 

I live in Georgia and the hurricane destroyed the roof.