That seems to work out fine though I'll need to make some decisions soon regarding replacing the furnaces with new ones or providing each unit with their own separate HVAC. 

As it turns out, this property will not work out, but we are on the case of three others already.

Yeah you can be leveraged 75% on every property but if it costs you $$ every month - then that isn't going to work out. 

How did that work out again?

We did that on this deal and made another offer, at that time the seller finally countered and we were able to work out a deal.

As a beginner investor in the Chicago area, it's really cool to hear about creative deals that work out like this near the region.

For the rent repayment work out a payment plan as to how much they will pay you back every month over the next XXX months.  

The numbers work out much better for us. 

Whatever he would agree to, obviously less is ideal for you, and then workout a 3 or 5 year amortization at an agreeable interest rate to give you room to run it for a few years while paying it down, then a refinance so he can cash out and you can get long term conventional financing locked-in.

The son lived on his own at some point, then he moved with them prior to moving to CA, things didn't work out, he moved back in.