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I’m going through this journey myself with a similar background, if you want to DM. Based on my analysis using the DealCheck App and Homesnap, Chicago neighborhoods don’t show positive cash flow due to high property taxes and depressed rents, appreciation is what you would be banking on.
I would also consider pivoting to Bridgeport, Bronzeville, Humboldt Park, TriTaylor etc since the neighborhoods you mentioned are somewhat saturated with low inventory (although high occupancy)
Good luck!!!
I would suggest looking at places where appreciation is likely to offset the high cost of carry (owning the property, expenses, taxes, etc. as has been mentioned). Logan Square, Pilsen, eventually South south loop. Otherwise, invest in some of the hotter markets where population growth is more supportive of long term investment. Happy to talk more to you and others!