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.

City and County websites 11.

So that rules out areas like City Heights / Skyline / etc.4) Parking - make sure you scope out the parking situation before you buy.

Cheap rates and modern tech are great, but none of that matters if they can't actually get you to the closing table.

My city does allow month to month rental.

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.  

I remember reading something in the Wall Street Journal the other day that buyers lean toward modern finishes with a nod toward sustainable materials.

You're not going to know the whole city from one visit but you may be able to identify and drive one or two strong "buy" locations for yourself.Best of luck!

I have tons of connections with people who do marketing all over the city I live in.

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.