+Find a local Realtor that works with investors, or a wholesaler.  

Hi Tricia, I'm interested in some mult family in Gary, and would love to have a local agent to work with.

It is very challenging to get your AirBnB license unless you are renting out YOUR UNIT or you do 25% of your units if you have over 6 units or something along these lines.The only way I'd advise STRs in Chicago would be if you are going operate a business to scale and had the resources/local knowledge to do so.I'd actually highly suggest Michigan because there is WAY LESS restrictions.

Check with the local lenders on financing it.

Long term opportunity in phenominal location How did you find this deal and how did you negotiate it?

As you prepare to invest, you might also want to connect with local real estate professionals who can provide insights and help you navigate the market.

Doubt they have any local market data to support.

It's not unusual to see 3/1 and 4/1 Section 8 properties but that single bathroom would not do well as an MTR.Overall, I'd say location and the shape of the property is going to be your key driver and the factors that will make or break you in the MTR space so very carefully evaluate both before you make your decision. 

Take a look at local banks though.

Be sure to connect with local investors at real estate meet ups and let people know what your investing strategy is.