Look for areas with increasing transportation infrastructure (Q-Line).

Due to the restriction in air flow it would create we did not reinstall it but left the furnace without a filter to prevent damage to the furnace.PLUMBINGThere is a cast iron sewer or drain pipe on the floor of the South side of the basement, there is an open clean out missing a cap or covering on this pipe.The drain below the bath tub was leaking/dripping during today's inspection.The service wire to the water heater is not enclosed in conduit or a protective covering to guard against accidental damage to the wiring or its sheathing.The water heater TPR valve is missing the extension pipe to the floor for safety.ELECTRICALThe house has some of the old knob and tube style wiring.

Have all tools needed and transportation.

Chicago with the abundance of 2-4 flats, access to public transportation, unique neighborhoods and strong real estate market seems primed for hacking.I will start a blog on Monday so I can organize myself and track my progress.  

I Attended New York Maritime Academy where I studied International trade and transportation.

I don't have all backgrounds of the property such as (Bedrooms and Baths, Property Tax, Principle & Interest, Neighborhood, Transportation Availability, tenant screening, etc.)From the advertisement it seems like the seller is trying to owner financing, if this is true does the Mortgage amount from the 50% rule still apply?

The point is that housing should be 1/3 of income because the other 2/3 of your income is needed for utilities, phone, transportation, food, clothing, entertainment and other expenses. 

In Chicago that could get you a solid $650-750k 3 flat in a B+ class neighborhood w/in about 30 minutes to downtown on public transportation. 

Is it near public transportation that can take you to the attractions?

Detroit is a "Future City" and as such is in position to stand out as the USA's version of what other emerging cities are experiencing in terms of growth, modern infrastructure, transportation, architecture, etc.