I purchased thru her as a realtor, moved to the location as my primary residence for a year (I travel/work from home), then turned the unit over to her property management company/team after my first year enjoying the unit.  

He said that he needs to find a 6 month rental for two executives that travel to Destin for work frequently.

I am thinking they could easily do the same.

Or are they there for vacation/business travel and have better things to do?  

My guess is this is motivated by 3 things:- Travel and bookings have got to be way, way down.

@Richard Weinberg1) If you have a Solo 401k that supports a 401k participant loan you can simply take a 401k participant loan up to 50% of the balance not to exceed $50,000.2) The notion of loaning funds from your self-directed IRA to someone else (and vice verse) could easily be challenged as a step transaction where the step of loaning to someone else would be ignored and the transaction would be analyzed as a loan from your IRA to yourself which is prohibited.

My heart is leaning OC given the family tie, obvious synergies with travel, etc. but my mind is leaning Tampa given the hard numbers. 

Right now inner city STR are struggling due to Covid and people not doing as much travel that is non vacation related.

I'm really struggling with how to determine what is the BEST FORMULA to determine/analyze a positive cash flow property when purchased price is higher, particularly bc I would easily need to put down 100k, not the 10-20k that some people need for low end markets!  

My cleaners supply their own cleaning supplies at no extra cost (although you'll want to supply your own vacuum, bedbugs can travel from property to property in vacuums).