Slightly complicating matters is also selling our existing home.

Power of Attorneys for ailing old people can get extremely complicated, and the entire transfer could be voided by a strong Elder Law attorney if the old person decides to renege and uses then existing mental condition to challenge the transfer.

I don't want anything complicated like AutoCAD or SketchUp.

My answer is a bit more complicated than it should be.

Many of these properties have complicated scenarios such as deceased owners, missing owners, judgments, etc. that require title-clearing and/or probate skills in order to complete the purchase prior to sale (or suction timeline). 

Tax liens are complicated in chicago.

It has nothing to do with who he is, the past relationship, or anything of that nature but rather the complication of a business transaction.

It is not that complicated, and this is a common practice in the industry even if you are raising money from the family and friends..You can actually schedule free consultation with one of the Gene partners (I spoke to Amy ) , and discuss all the issues/concerns you might have ..

There are layers and layers of analysis and critical decisions in the questions you have both posed and how it should all connect together and layers of complications that you are not even considering.

This could be another great answer for you but is a bit more complicated and costly.But in essence yes, there's several ways to go forward for you.