Don't overlook the importance of knowing the rules, ensuring utility access, and researching the potential return on investment.

I believe the property has potential, but it is going to be major.

I am interested in potentially investing in the South Side of Chicago as well.

I’d love to partner with someone and potentially go in a multi family or multi unit property!

Repairs & Maintenance (5-8% of rental income)Take a look at the BP rental calculator to see all the potential expenses you may have while house hacking. 

Understanding the potential value of your property you can then start researching the potential for doing a HELOC & know how much you can pull out of the property to support the strategy of purchasing another home for either a flip or a rental4.

as far as financing will go for your potential buyers the duplexes will be easiest because you can get both investor and owner occupants . the multi family 5 units and more will be cinsdered commercial and cut out owner occupants . the assisted living is extremely limited when it comes to financing and now it becomes a specialty item that's an investor looking to be in assisted living business 

I'll echo that most of these Midwest markets that skew toward lower purchase prices are similar.Areas can be hit-or-miss and you need to really understand the risks and potential rewards before making the plunge.

Peace ✌🏻  You have the potential to earn more money if you do the rehab, source the contractors, determine the ARV etc.....You also have a higher risk of failure.

A good agent will shrink your learning curve and help you avoid potentially very expensive pitfalls.