Quote from @Veronica Mitchell:
Yes, I'm looking at 4 plex units renting the three and living in the other interested in the more up and coming areas. I'm interested to know because you invest in the South side what do you see as the perks in the future investment there?
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The fact that you are looking at "up and coming" areas tells me that you put more emphasis on appreciation than on cash flow. That's fine. Seeing as how in today's society the rich get richer and incomes aren't keeping up with the stock market, people in rich areas can afford richer rents. Given that birds of a feather flock together, I think you're looking to live almost-rent-free whilst coining it on appreciation. Am I right? You may pull it off.
Still, there's something to be said for the critical mass, many baskets, safe-if-boring neighborhoods. The South side of Chicago abounds with those. Chosen right, some of those South side neighborhoods may become hot, and give you large amounts (percentage-wise) of appreciation. How, and why, do you select them?
First, look for market inefficiencies. One of those inefficiencies is race aversion, if not outright racism. That means that you can buy a house on the South side -- identical to one on the North side and in its doppleganger (save race) neighborhood -- for literally a $100,000 less than you can on the North side. So an identical neighborhood (income, crime, school quality, etc.) can cost you as much as a $100k less on the South side simply because your neighbors are brown or black as opposed to white.
Second, look for infrastructure similarities. Proximity to mass transit (mentioned by another poster re following them), proximity to downtown (maybe not so much now with work-from-home being a thing), proximity to airports, highways, pollution-belching industrial plants, hospitals, universities, the lake, etc., all help to define which South side neighborhoods have what it takes to overcome market inefficiencies and become "up and coming."
