Apparently, Chicago/IL landlord law requires regular payments and/or accounting of interest earned from security deposits, and failure to follow through on that can result in a fine of treble the amount of the security deposit. 

These have a high failure rate because one of you can just walk away and the other is stuck with the debt.

Other crimes that come to mind are brokering real estate without a license, real estate fraud (aforementioned and also possibly failure to disclose), forgery (creating fake leases), grand theft (taking money for rehabs and not delivering materials or completing work), wire fraud, money laundering (operating a Ponzi scheme), etc. etc. 

Drug dealing 4 times , assault and battery 2 times , domestic violence 4 times , IRS lien over 10K ,  failure to pay child support 10 times , and only 1 Failure to pay rent .  

Can anyone recommend a lawyer who represents buyers who may have been defrauded due to the failure of seller to disclose known problems with a property prior to purchase.

Not RE related but it makes you think different in that you’re fully responsible for your success (or failures).

You could do the lease option and then when they default you would have their deposit but that is not exactly honest.Do not do it, it is a recipe for failure.

(c) No cause of action shall arise against an appraiser of real property, a licensee as agent of an owner, or a licensee as agent of a potential or actual transferee of real property for failure to inquire about, make a disclosure about, or release information about the existence of any fact or circumstance or suspicion of the existence of any fact or circumstance that indicates that the real property is psychologically All that being stated, I'd leverage the heck out of the situation in dealing with the bank...

I have very high integrity and fully believe that I am responsible for the outcomes of my life, rather than blaming others for failures. 

A vague foreboding that it could all go terribly wrong, that you never really know, that one day we could get a call that the whole building had gone up in smoke, or a giant sinkhole had opened underneath it, or a particularly bad windstorm had flattened it, or bad wiring caused one of the tenants to be electrocuted, or, or, or...We are all afraid of failure, and worst of all, failure right at the beginning of something, a failure that completely exposed our incompetence for all the unkind people we all know to laugh at behind our backs.