I do feel I have a lot of skills that I could offer that I have built from my current W-2 job.

Personally, I don't like condos- HOAs and surprise special assessments can eat up any potential profits and in most states, they can just change the rules when they want to and decide that LTRs or STRs are no longer allowed. 

I'm another Mansfield person and I'm always looking to connect with other locals.

@Nathan Gesner Thanks Nathan, you are always so helpful when I post a question on here so I wanted to come back and personally thank you and post pictures of the issue being fixed.  

You would then periodically pull the ap up and "swipe left of swipe right" for business or personal trips.

You'd do better just driving a neighborhood (a lot) to get the feel.

In my past professional life I worked as an attorney for a hotel development company that owned over 1B in assets yet as a company we  did not feel the need to utilize entity structures nearly as complexed or  convoluted as what you arranged. 

@Alex GarridoInvesting in Panama City would work out for short term rentals because you could pay for the holding costs and maybe profit nicely while hopefully the value of your property increases over the long term.Unfortunately, it’s illegal to rent for less than 45 days and personally I’d never suggest anybody gets into an illegal business overseas.I’ve come across a couple rare buildings in Costa del Este who have a permit but, as you could expect, it’s reflected in the price.

I own 5 cabins and I have never had any issues with them personally, going back many years.

1) Specifically looking at the midwest, I personally am doing a lot of business in Ohio.