It has been maintained pretty well but my gut is telling me that it could easily turn into a money pit.

I've always thought (I may be wrong) that they were difficult to get and to maintain the requirements.  

She stated that the renter makes it difficult to show the house, and she may have to come up with money to sell it because of sales costs and comission.Her other property is in Ohio, she had purchased it in a tax auction, but never had enough money to fix it, so she has been accumulating property taxes on an empty property for six years.So I gave her a plan to sell both properties immediately and she was able to even make some money within sixty days of putting the plan in effect.

When I spoke with 2 of the 4 tenants they said maintaining temperatures in the unit was not a problem. 

I think direct mail is the most effective, particularly driving for dollars in your target neighborhoods.

It may be worth to research other Presidential Libraries and see what's the effect in the areas.Washington Park connects to Jackson Park through a  nice boulevard.  

If I were you I would self manage especially if you are only cash flowing a couple hundred and there are only 2.Plus it gives you experience in the field and once you acquire enough to hand off you will know what needs to be done and will be able to manage you PM much more effectively.

I agree with @Leo KingstonAbsent a pre-death transfer by the decedent, it will likely require probate to effect passing marketable (insurable) title to a third party. 

I think the most effective tool is YOU.

It will be a lot cheaper and more effective.