But if you have a cash buyer who is specifically looking for income property, and even more specifically a vacation rental property,  I firmly believe that there is a value add from having a working STR there.

We want to be traveling and sailing throughout the year, not just when a job allows me to use my 10 days of vacation.

We've got great reviews and super host status on a personal account, but we're planning on building a brand via our management company and buying cabin communities / boutique hotels as well.

Airbnb already became a synonymous for family vacation.

I also got a written and signed agreement from tenant that is notarized for him to vacate on or before 2 weeks deadline after closing. 

The company managing our property as a vacation rental was unable to get the power turned on in our condo for months because we had to get the meter switched into our name with the electric company (which is much more difficult to do in CR than in the United States).

Quote from @Collin Hays: I visit fairly often with investors looking at a certain vacation rental property to make an offer on.  

I typically plan for 5% of my rents to be saved for vacancy.

We have one property already as our primary home with a plan to buy another house and rent out this one.

The demand for vacation rentals in places like Destin, 30A, and Panama City Beach remains strong.