If I fund the reno (during my lease period) and I don't end up purchasing the property, I will be out a great deal of money without receiving the reward of my extra investment.

Tom Anderson if in doubt about a contract or even a bid price, pay a lawyer you trust a few hundred to negotiate the different bids you have received.

I also received your direct message and will correspond with you further on there. 

My plan is to get the list into excel, filter by target area and find out assessed values for properties using the assessors' website.

In addition, they are either 100% occupied and receiving rent or 100% vacant and a big expense, where a duplex can be 50% occupied and when you have turn over or a non-paying tenant you still have some rent coming in.   

You are the one receiving the payments.

How can I become a court appointed receiver in the state of Illinois?

If student never takes title and parents pass away, student will received a stepped up basis in the property at the time of death meaning that the student can then liquidate without paying a cent in tax. 

This property currently has 4 tenants that are receiving USDA voucher assistance.

Billy Smith Billy this is great feedback, this sounds very similar with some of the advice that I've been receiving from people close to me!