That person could be one of the heirs, a trusted friend of the deceased, an attorney, etc. 

Get their names and numbers and email address and tell them when other deals like this come dwn your pipeline they will be the 1st to kno.

As far as the Lease/Option solution is concerned, I could address all of the issues here, but it isn't needed...because the whole L/O option stops before it gets started. 

Land contract, CFD or note and deed of trust/security? 

I don't even need to know the address or look at it, if its west of Kedzie, $150k for a 2-flat is too much in my general opinion.

This was a long term tenant who I like and respect, it was fun to show her my trust and support. 

Try Hometown Savings, Webster 5, Rockland Trust.  

The hard parts are setting up the relationships and trust in that team necessary to be able to execute on the plan, and making sure that the deals still pencil with all of the people involved. 

@Shane H.We'll have to close some gaps in your story and address some basic concepts before arriving to an answer.1.

Text him something like "water is coming from under your door...if you still live there please let me know and handle it otherwise let me know so I can go in and address the issue."