Where should I invest next?

[Ryan Peach]

My goal is to "retire" in 5 years. I want/need roughly $8,000/month to cover my current income and benefits. I live in Evansville, which is growing but still a small/mid market. It is currently saturated with investors and housing prices are crazy high for the area. I live 2 1/2 hours from all of the following: St. Louis, Nashville, Indianapolis, and Louisville. I'm afraid if I wait for the market to settle here I won't be able to reach my goals. If you were me where would you try to invest next? I have 2 local rentals now, have flipped in the past, and like the idea of Airbnb.