Hey @Mordechai Chaimovitz - It sounds like you are talking about Chicago's NW side because there are definitely tons of areas in Chicago where a 2 flat can cashflow well.I know for me buying on the nw side was critical to my personal well-being and life happiness. 

I’m personally based in Houston, TX, and I’ve noticed over the years that a good realtor can do a lot more for an investor than just listing a property.

First of all, my personal credit was a very good at 735 midscore. 100% financed tidied it up just a little bit more with  just cleaning up a couple of things on my credit.

This is from personal experience, the housing authority is the problem.

During this 24-month period, the property must be rented to another person at a fair market rental value.After the 24 month period your sibling could convert it into a primary residence.

Best regards, This approach is neutral and objective, focusing strictly on the criteria, and avoids discussing any specifics about the applicant’s personal situation.

I personally did a couple last year that I self furnished and self manage while working full time.  

Yes, as I'm doing more research, I'm finding that I would prefer to invest in markets that I know personally, so as not to rely on external variables completely.

Generally there are multiple units for each "zone" if you will when I've seen them installed.Regarding your problem at hand, I personally would simply adjust your plan to move and make your initial plan to get the current issues resolved, while costly now, in the long run holding onto the unit will likely pay off. 

Personally (as a STR-focused REALTOR), I would never give you numbers and tell you you can hit them.