I don't know that I would work through a title company for issues that could be more involved like doing quiet title actions, paying estate taxes etc.

So the good news is that there are currently two full-amenity condo buildings in/near downtown Chicago in prime A+ Class neighborhoods that allow short-term rentals: 545 N Dearborn and 30 E Huron.

If you can get 10 or 20 landlords to kick in $100, you can have a lawyer review the docs and laws and regardless of the review, send a letter threatening legal action. 

A contractor violating this law is subject to disciplinary action including possible license suspension.

You allude to actions that sound them being a wholesaler, but you also mention them wanting to be investors.  

The great news is I have the time, knowledge, resources, and critical thinking skills to bring these projects to fruition.

Be honest, take action, and trust the process.

Search the County’s Prothonotary Office Purpose: The Prothonotary office handles all legal cases related to property, including court judgments, liens, and other legal actions.

The good news is that once you gain some traction you can hire a VA to help with the initial calls (either part time or full ). 

Now it’s time for action.