The first thing I want to point out is that it may be wise, in your thinking, to separate the property itself from the STR business that's being run from the property.In the old days (as recent as 10 years ago), people buy a vacation home to enjoy, and they leave it empty when not in use. 

Plus you can use it for enjoyment over the years..

I purchased both as a package and for the next six years enjoyed great cash flow as I paid the tax on the house lot annually at about half of what it should have been and neglected to pay anything on the tennis court lot.  

Congratulations, @Glenn McCrorey Enjoy the fishing!

I lost money for many years in real estate, while my friends were enjoying life with their savings.

Seller financing means I enjoy 30% ROI YoY.

An experienced agent will list your property with the language, "no showings until an accepted offer", to avoid violating your tenant's rights to the peaceful enjoyment of their home - possibly resulting in their lack of cooperations and a lawsuit against you.

I recommend you figure out what you want to do, then actually do it to see if you enjoy it, have some skills, etc.

My primary business is owning a wealth management company, and is where I enjoy spending my time.

Enjoy that well earned retirement.