What neighborhood of Chicago and how large are the buildings?

Try looking into zillow/Redfin and see what your potential rents you can get near the neighborhood by filtering the bedrooms/bathrooms of the intentional property that you are planning to buy.

Furthermore, the State has put together a task force of prosecutors to put a dent in organized retail theft.

B- area or less, the sign notifies the neighborhood thugs that the house is vacant. 

You'll get a feel for the age of the neighborhoods, the vitality of the commercial buildings, the ease of location, the closeness to jobs.The markets you're describing are more linear, and usually have lower capital appreciation.

@John Matthew Johnston 80% of the time, it's a thankless job:(You're never fast enough for complaining tenants, nor fast enough or cheap enough for owners.To have any chance of success, you have to be extremely organized, or every day starts with your hair on fire!

The location is ideal, as it’s situated in a neighborhood that permits short-term rentals (STRs), making it a great investment opportunity.

Every Market (Detroit) is made up of a series of Micro-markets (neighborhoods) of which they are all different in cost, value, cash flow, rents, etc...

@Allison Littman To structure the purchase creatively, you could split the $600k transaction into a $400k purchase agreement and a $200k charitable donation to the seller’s tax-exempt organization.

For example, intro's to people here that can help you with certain specialties, planning, feedback on neighborhoods, financing of course, etc.