A major negative is that when you strip away the industrial era attributes like water transportation, hydro electric power, relative cool summers ( an industrial neccessity before air conditioning), a semi skilled work force, and the advantages of having a geographically concentrated industry, you are left with a city with a high level of poverty, a low level of education, a corrupt and ineffective government and very bad weather.  

At some point they enclose the porch, and then they finished the space.You wouldn't ever suspect that it used to be an exterior space, but once you realize that it was, the slope makes perfect sense.

My background is in the transportation sector. 

Only 1 out of the 10 that showed was actually licensed but he was mentally unstable, to say the least...Most that showed had no transportation and/or drivers license, they had a family member drive them to the site. 

Transportation is always a good thing for rentals, and values are low over there right now.

I just started out on my career as a transportation engineer, but I'm finding there are other avenues to creating income.

Lastly, in your opinions, does having a property with a driveway to park a car a necessity or luxury in these areas (close to the city with public transportation)?

Close to restaurants, public transport, attractions.

And boxing, transporting everything as well.

Specifically, Illinois has a huge talent pool of highly skilled workers, world-class universities, more money for investment, and better transportation with an airport with direct connections around the globe.