@Paul Winka - Though it may not be required in your state or local jurisdiction, it would probably be best to hire a licensed/insured contractor to do this work and hire an engineer separately and directly to do the analysis/design.

I've put together a quick proforma and I wanted to get some (semi-)professional opinions.Case Study:Cash deal (no financing for purchasing/rehabbing)Asset ~$20,000; Rehab ~$3,000; Closing costs/fees ~$2,000Total out-of-pocket: ~$25,0002-3 Bedrooms, 1-2 Baths; Rent $700-$850Annual Gross Revenue: ~$9,000Property Tax ~$1,500; Property Insurance ~$1,000; Property Management ~$1,000; Vacancy Loss ~$1,000; Replacement Reserves ~$1,000Annual Operating Expenses: ~$5,500Annual Net Profit: ~$3,500Cash on Cash: $3,500/$25,000 = 14.0%Risk Profile:Rental properties in low-income areas carries the risk of vacancy, damages, delinquent payments, and evictions.Risk Mitigation:I see paying a Property Management company as being a great way to help with: sourcing the most reliable tenants, bi-annual interior/exterior inspections, and handling the delinquencies/evictions. 

Est 233 ,, divide by 4 = about 58 each.. hard to compare the duplex you didn't include price,, so ya do the math but personally I put my efforts towards the 4 plex.Honestly if the guy is 100% rented and his rents are close to market you can figure the interiors command that price and are probably pretty decent.YOu can start this property and do very little until you have a vacancy, and then decide what you want to rehab, otherwise  your set, and can do some exterior, yard and common area fixes first which will attract and warrant rent increases to current units.

I've been an Estimator and Assistant PM for a GC, performed take off for a large government construction management firm, conducted design reviews on behalf of the government, and I am an Architectural & Civil Drafter by trade.

Pillow is specifically designed to offer short-term rentals as an amenity.

We also seem to have similar backgrounds as I have a mechanical design engineer background.

But I am an interior designer (I work at a local architecture firm), and I'm willing to help with any interior design or decorating issues/questions you may have!

Or was it just that the the property wasn't maxed out for the zone that it is already designated for?  

Then I look at the condition of the propertyA = Brand new constructionB = 1975 and newer homes with a FULL renovation (Roof, HVAC, Appliances, All hard-surface floors, Exterior and Interior cosmetic repairs and paint, Hardware replaced, New light fixtures, Fenced in Backyard, and more!)

Those income limits were enacted because cook county was declared a designated disaster area back in 2013 by FEMA.