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. 

Some people are still in their work suit attire, while some people are dressed down.

We bought the house three years ago because it was closer to our kids' private school, but it coincidentally had a rental suite.  

I think the most effective tool is YOU.

It will be a lot cheaper and more effective.

You will network with people who offer tips on refinancing, good books, effective classes, ect.

If you don't you've effectively reduced the security deposit you hold by $300.