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. 

Paul, the deportation efforts aren't overly concerning personally because the few assets I have left in my current portfolio don't have a high immigrant resident profile (nor do the submarkets).  

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.

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

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.

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

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. 

I haven’t done my first deal yet, but through hiring a local contractor to build my personal residence I had this idea that I don’t hear people talking about.

@William Taylor so many options...Use your RE knowledge to: WholesaleFind rental deals to sell to investors locally or here on BPStart leveraging your personal contacts to build your sales businessFind a motivated seller willing to do seller financing:- Move in worst room or basement, rent out all the other rooms for max cashflow- You could even live in the basement and STR the rest of the house

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.