As Chattanooga grows, these areas are becoming more and more desired.

(There is in my market) Is there a smaller sized property that is maybe only 2 bedrooms and less desirable but more affordable? 

Pro-Tips; Set up Zillow alerts for all multifamily units for rent in the desired area and call each new one that comes up. 

And it is close to a lot of desirable amenities in town, despite it being a lower income part of town. 

Citing that piece of true information gives no information about the desirability or value of Chicago's real estate.To even make any generalized statement like "Chicago is undervalued" is ridiculous.

I would start loading up on as many real estate and mortgage classes that will fit in your desired niche as possible. 

That could be your quickest way to get into one of the markets you desire.

They are located in the most highly desirable neighborhoods, with the best school districts.

We've seen this broad pattern before, nationwide, it takes a decade or more to pan out, and each time everyone scratches their heads and accts like we've never seen anything like this before (often times there is some unique, event or cultural shift, that comes along and "tips the scale" this way or that, which I think is about the only thing unique to each one):- urban core deemed more desirable (1920s, 1940s, 1960s, 1990s-2020[?])

Tenant can add 240V service if desired.