Paid Off Rental Properties: Next Options?

[Donald Aleshire]

Hello,

This is my first post on BP and excited to become a regular users! I have been reading a lot of books on Real Estate investing and methodologies, listening to the podcast's on BP and going to meet up groups to learn more. 

My question is in regards to rental property that my father owns and what the best options for him may be. 

Background: My father owns 4 different properties in the south suburbs in Chicago, all 4 properties are paid off. 3 are currently single family rental properties and 1 is a residence for his family. Of the 3 rental properties, 2 are occupied (renters somewhat paying rent) and 1 is for sale (been for sale for 12+ months). The house's current market value have been appraised for roughly $30k - $60k each. (All different sizes, bedrooms, conditions.) 

Ideas: 

My father is 74 years of age and still working but plans to retire within the next year. The family plans to move to another suburb and retire all together. He is having issues selling the houses due to several reasons. People in the area can't qualify for a loan, the neighborhood itself isn't desirable and he has sentimental value tied to the houses. 

I am not in charge of these houses but I want to evaluate the opportunity of these properties if done properly. Because these are paid off, there is some potential but I am not sure the area of Chicago offers much. Below are two of my ideas:

Property Manager: determine a property management company for the South Suburbs to help manage/run the property. Cash flow the rental income since these are paid off without any of the headaches dealing with the local tenants. I have a friend who does contracting work who I could ask to do the contracting work if needed. 

Donation: since my father is still working, he can use the donation of the houses as a tax write off to his income. This would be the easiest of the solutions but I do not know much about this from my studies/reading. 

Feedback/Ideas: This is my first time posting on BP but wanted to throw this idea out to individuals on the forum to get some ideas. Feel free to ask away for questions so that I can provide additional information. Thanks in advance for any help.