I don't own a STR, but I stay in them whenever I travel so I can offer you some perspective from the traveler's side of things.

Listen to others who have traveled the same path as you.  

Travel, not having your password list with you, a forgotten laptop and family obligations help create huge windows of time for thieves to charge and charge and charge, uncontested.

I hate moving it is the worst.Yea born and raised in Chicago and then I traveled working for a major general contractor for 10 years. 

Houses sell the best during the spring and early summer months and travel/tourism is pretty good year round but much better in the non-100 degree months.Since you're going to the midwest, properties are considerably cheaper and cashing out here can probably get you a few rental properties you can self-manage once you move.

I have no qualms with renting out the entire space while living in a trailer in the driveway - going the aggressive house hacking route here!

My end game is having enough passive income to cover living expenses, travel and giving/donation objectives I have.

I found the deal by asking my best friend's mom, "who owns the trailer park in town?"

Obviously AirBnB is here to stay, but from my anecdotal evidence, people are itching to travel further (especially international).

Seems like a good idea, especially if you have a travel reward or cash back type card.