I purchased my first two multi-unit properties using data and they've doubled in value in 5 years simply because my metric was population growth and movement. 3.

There are a lot of variables to consider so it's impossible to say if investing in one of those other markets would have been "better".However, I think you could make a stronger case that you have been (or would be) more successful with your real estate investing in Chicago compared to other markets.

I mean just look at the cheapest rental properties in your area or our area .. and compare them with mid range or higher end ... which would you prefer to own and which do you think are more safe and consistent

I STR it for 15-20K a month in the summer, and was offering it for rent for $2100 a month in the winter (lower than any comparable houses), and was getting tire kickers at that price. 

A HYSA is a type of savings account that offers higher interest compared to traditional savings accounts!

It would be great to compare notes - how do you feel about expanding your search radius or even considering new-build opportunities further inland?

This allows you to compare prices quickly.

I'm looking into purchasing a rental property in the Belmont area of Dayton, OH and wanted to get any insight for this market as it seems concerning that the average rent is higher compared to the actual costs of houses in the area.

Then compare that with your normal 30-year fixed.

Ponts can be built into your rate as well so compare notes with more than one lender/bank.