I am originally from Germany and the last ten years I was mainly travelling around the world and working in all kind of different fields to find something I love doing.

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.

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

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

I am thinking of Austin, TX and Southern Florida (Ft Lauderdale, Plam Beacon) but with inability to freel travel due to covid, knowing someone trustworthy on the ground is more important than ever and that's what is holding me back right now.

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