You will loose square footage because the walls will need to be 6", and you will need 6" insulated on the floor or perimeter insulation, which might necessitate raising the roof.

You will not be allowed to rent the building until that is completely so whatever you do don’t loose your tenants because you can’t rerent if the move out!

. - Why in the world didn't you just tell him - I'm sorry, you are bound by the lease you signed until X/X/2020. 

I recommend setting up keyword alerts for each area as they are discussed in the forums daily with advertisements posted in the BiggerPockets marketplace hourly.One thing to note when looking at the individual markets, you can make or loose money in any market.

Agent365 etc have lead sources.Again you need to skip trace the owner and SMS / direct mail to these owners.3) the hardest to deal with are pre foreclosure owners.  98% of pre forclosure owers say they want to keep their houses,,, yet they are 4 weeks from the auction of loosing their homes. 

I was loosing hundreds if not thousands of dollars monthly when I joined.  

Currently one condo that my friend owns the board decided the windows aren't good enough and doing a 25K assessment per apartment...knowing that a chunk of people are going to loose their homes but they don't care.

Anyways, back to Chicago, I have been there a few times, although mostly d-town and north-bound (Wrigley field area)... to me it is world-class, beautiful, clean, rich, affluent, safe... but I am aware of 'what they say about the South'Yes, I am from Canada, and no, I do not 'understand' what a rough area is... a random mugging, kidnapping or murder here is simply unheard of... in a 4million ppl city.Social net is much higher, you will never go hungry here, guns are pretty much inexistant.

So if you convert this property  to a rental for the long term,  you will loose this benefit.For rental property, I never plan on paying a tax from the increase in value under the current rules. 

The property looses money starting on day 1 and will never have any appreciation to change this.