Not surprisingly, this led me to class C properties. -- For this buy, I wanted 90%+ occupancy rates.

So, why not purchase something in the middle of that range you mentioned, in a working-class, up-&-coming neighborhood?

I'm looking at a property that is listed as a 2 flat; however when I went on the chicago zoning website, the zoning class is B3-1 which does not make sense since there is no retail currently.

Your $100k is your 25% down payment and hold back some initial reserves and closing costs...find the market that meets your criteria for a C-class value-add MF property, build your team (starting with an agent), and pull the trigger...long-term buy and hold...drop all profits back into renovating units and forcing rents higher...take advantage of your equity in 4-5 years and buy another one.

The recommended entry budget is the starting point for your investment amount where you will begin to find a profitable short-term rental.Panhandle–Beach destination; somewhat seasonal; recommended entry budget: $500K South West–Beach destination/snowbirds; somewhat seasonal; $400KCentral East–Beach and events destination; seasonal; $280KCentral West–Beach destination; mostly seasonal; $400KSouth East–Beach and resort destination; year-round rentals; $500KCentral–Theme park destination(events/resort/family); year round market; $300KFlorida Keys–Beach, boating, fishing, family destination; mostly seasonal; $500K

Obviously there were some caveats there... we didn't want F class properties, and we wanted them to be in at least descent condition.  

Further south into Brookpark and Parma, there are probably more working-class multi-family opportunities. 

Is the project a Class B value-add with minor improvements to reach B+ /A?

They are bought and sold just like a car or boat.

I wouldn’t lower the qualifications for your tenants, it’s better to wait for a class A tenant than rush to fill the vacancy.