The folks around Table Rock Lake seem to have it all with both the nature amenity and entertainment nearby.  

I think B-/C+ type stuff is the place to be, and Chicago is full of C class buildings in solid areas with a Chipotle or Starbucks nearby. 

@Joshua Jones - We could help if you were a little further north in Chicago.I'd suggest plugging in a couple more cities that are nearby to see if those keywords get the attention of other investors in your area that might have some good contractors.

Facebook Marketplace, Craigslist, Realtors who have closed similar sales nearby, other wholesalers, builders, recent cash buyers in the area of similar properties

It does use real data from nearby properties on Airbnb and VRBO, but sometimes the comps aren't great.

I'm interested in investing in MN/WI/SD/ND/IA/NE as I know a bit about the areas, and have friends and family nearby that I could partner with in the future.

There are a bunch of Airbnbs nearby.

The one thing I like about investing in the city as opposed to the nearby suburbs are the lower property taxes. 

A nearby city they made them illegal and people where doing them anyway.

In FL you might also be able to find a "vacation home" nearby and get short term rental income.