My wife and I have been flying down from Detroit since 2012 to attend Lifestyles Unlimited events right in your backyard. 

Then you'll need a good property manager, who has access to good maintenance people, coz you're not gonna want to fly out there to fix toilets yourself.If the numbers work out, and you can rely on your team, there shouldn't be any unmanageable difficulties.

That's when a buyer's agent's experience comes in, they know the market and know that some low ball offer isn't going to fly.

I'd like for it to fly under the radar and to be able to rent it out on airbnb with a Short Term Rental Permit; but not sure if I can reliably do that.

I'm looking to show up in Dayton over a weekend and look at properties and hone in on the things I need to know (which areas, local stats, etc) as well as refine the search for the agent, but afterwards I'm not flying up every time a new listing pops so we will need to work out the long distance thing. 

The reason is that he wants to spend more time with his kids and fly his plane.

I am new to the investment arena but ready to jump in, located in Tampa, FL.  I

Heck, you may even have to fly down to a different state to get a feel of it, but I wrong strongly suggest that you get out of your comfort zone, and see what other markets are out there for you.

Quote from @Chase Hoover: Listen to recent BP podcast 604 - best 45 minutes you can spend today!

There were lots of db's in when I was in, some who end up getting processed out on BCD or DD, some who end up flying under the radar and retiring with a nice pension.