It's important not to get too caught up in the details; use the analyzer to compare one property to another.

MTR arbitrage may allow an owner less hassle and equal profit from their unit compared to the other available alternative of LTR.3.

Additionally the suburbs have higher taxes compared to Chicago proper.  

This typically means lower down payments and better interest rates compared to traditional investment loans.

Understand the fees involved and calculate the total cost for an entire year of management so you can compare the different managers.

For example, if you are in a secured position and invest $25k and can get 10% per year at $2500 or you can get 15% unsecured which is $3750, are people willing to risk the extra $1,250 a year where you could lose all of your $25,000 investment compared to being secured where chance of losing it all I would view as astronomically lower?

You're spot on with how private money lending offers speed and flexibility compared to traditional banks.

Then you get stats on all these things showing a unit was "on" all the time and can compare to temperatures in and out of apartment.

Do one task at a time in each app so you can compare apples to apples.Load a property with pictures and details.Market that property.See what your marketing looks like from the public's perspective.Submit a fake application to see how easy the process is.

I agree with @Patrick Franta and @Mike Neubauer that  a 1 bedroom will give you a better ROI though because you can still find relatively decent deals on 1 BRs compared to 2 Brs.