You should connect with @Brie Schmidt as she knows and understands the Chicago zoning laws, but my gut instinct would be that you would be better served looking into a duplex down scenario.

You could be eaten alive without knowing for months.

The employer knows they won't report it to anyone for fear of losing their job.

Know your #'s, cut the fat, focus on quality. 

Then you can start seeing other places just on the MLS when you get this strategy down and knowing what rough numbers will be, but it is always mandatory to get a full amount of rehab costs to get the GC into the property. 

I.E. you know the area better than others.Is there a short-term rental market where you vacation at, where you went to college or where you grew up in?

Can you please let us know why you want to invest in Section 8?

I was considering the hard money lender route but got slightly overwhelmed because of the different options, rates and not knowing how to properly vet them.

You might want to speak with the owner of the house next door and let them know you'd like to buy it.

I agree with you that they would usually be better off buying in A and B neighborhoods unless they live locally and know what they’re getting into.