However, it would provide us with the necessary funds for the repairs and potentially a down payment on another property.

Ideally, it's best to have reserves before acquiring a property as it shows financial responsibility to potential lenders.

See Vacant Building Ordinance and registration form at https://ipiweb.cityofchicago.org/VBRCN193029Maintain watchman from 4:00 PM to 8:00 AM for vacant and dangerous residential premises. (13-12-140)CN193019Repair or wreck dangerous and vacant residential premises. (13-8-100, 13-12-125, 13-12-130)CN193000Maintain building in safe condition so it does not constitute actual and imminent danger to public. (13-12-130, 13-8-100, 13-12-120, 13-12-125, 65 ILCS 5/11-31-1) Maintain building windows and doors in safe condition. (13-196-550) Maintain stairway and porch in safe condition. (13-196-570) Maintain floors, walls, and ceilings in safe condition. (13-196-540) Maintain building in safe condition.

I went to all of the owners and was clear and honest with them about their current returns, expenses, ROI and potential future returns, every single one of them transitioned out of that investment class.

The owner financed position is a potentially zero interest loan that should be considered.Another quick note: consider leasing his land with an option agreement as well.

But sounds like you have more due diligence to potentially do.

Based on current rent not potential rent max price should be 900k to be able to cash flow property. 

Focus on the numbers, finding/buying/creating an opportunity, and maximizing the potential.

I'm with you @Noah Laker , I think there is huge potential in college towns and mid-to-large cities so long as you do your homework on the legal side.

Does not matter from whom you borrowed and where they got the money to lend you.Third, their situation is potentially problematic.