I know that I will run into issues and problems that will hurt my budget....

@Dan Marshall the tenants are protected by their lease, so the two issues re selling now would be inconvenience of showings for the tenants, and whether the property will fetch a higher price as a retail sale (as you suggest) or as an investment...I'm with you--if it's more valuable to a homeowner, you might want to wait it out....or, you could cash for keys your tenants and sell sooner.

I always assume there are issues and do my best to look for them when I'm there doing my inspection.

Its embarrassing (and unprofessional) to approach someone about solving their foreclosure issue when none exists and these owners won't be very kind when responding to you.

Ask questions about dealing with landlords, leases, tenant rights and other important issues."

Is this an easy fix or is this something that could get pricey the issue he has is the 2x4's supporting the roof. any input from experienced carpenters is much appreciated. my dad has incredibly high standards for things so i am trying to get a second opinion.

Personally I see charging tenants for repairing tenant caused issues however maintenance repairs are exclusively the responsibility of the investor.

However, he was responsible for showing apartments, handling all repair issues, seeing that rents were paid on time, keeping the outside areas and hallways clean, etc..Because he was always "on call" 24/7 (and my mom was expected to help out with the cleaning) he was given the basement apartment to live in rent free in exchange for a small salary (which is why he managed three buildings; one would not generate enough income for the family).Perhaps your applicant doesn't want to live in one of the properties he manages.Gail

Most municipalities are forgiving when you a buy a property and inherit these issues provided you take care of them quickly but you already own this property, they may not be forgiving

That’s a Local specific zoning/use issue.