Owensboro, the state's 4th largest city, has a population under 100K, and many OOS investors prefer cities with at least 300K residents and strong job growth.

Quote from @JD Martin: Quote from @Jay Hinrichs: Quote from @Matthew Drouin: Small wine town is all I needed to hear.Seasonal tourism is usually not a great industry in which to build a sustainable business.There are probably higher and better uses of your capital near high velocity metro areas.We have small wine towns near our city in the finger lakes region of western NY.  

Do you want to get into what can be a years long battle with multiple parties, including our darling city council, until you get to move into your home the way you want it?

Definitely better schools in Rockwall, I think more people commute into Dallas from Royse City than Rockwall too.

Do you have a specific area/neighborhood of the city where you are looking to househack? 

If any of your properties are discovered by City officials to be unregistered, you can receive an administrative citation for failure to register; this penalty can cost $100 or more per property.

Market Growth: Texas cities like Austin, Dallas, and Houston have experienced rapid growth, but is the market becoming oversaturated?

City and County websites 11.

I agree with Alecia-I would start with something smaller, find an city/area of town you like. 

My city does allow month to month rental.