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

., and potentially delay the SFR purchase plan according to the status of the investment.It's a hard decision to make since the economy this year is a bit flaky.

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.

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 

Keep in mind by building and then selling the home you are going to be taxed at STCG (effectively ordinary income) whereas the land, could be taxed at LTCG.

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. 

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

Renting modest homes/units is a large part of why my portfolio is resilient in a down market as well.As I said last week, take some time now to improve / harden your properties to remain robust against any potential downturn.

When applying for a DSCR loan, lenders typically assess the property's income-generating potential and calculate the DSCR to determine the borrower's creditworthiness.

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.