These units are rare to pop up (I stay in one of the units each Summer) and usually are gone in a week....so I know the opportunity is 'there'.The goal is to relocate in 4-6 years and use this as a primary residence (but still travel and use as a vacation rental).I'm confident w/ the rental history of these units and comfortable with cash flow (hate having to initially throw down so much $$......but HI has their 'rules').

Traveling to SE from NYC is inexpensive compare to Midwest or West coast. 

Also, I travel a lot in my primary profession so I have no issue with vacating my condo and finding another living situation (maybe a small apartment) if I'm able to develop a passive income stream by doing so.

I've stayed in AirBnB homes when traveling for work; the company paid the bill and we were surely very gentle on the home and furniture during our stay (who wants to have THAT conversation with your CEO?).

The same factor applies to travel to that location.

You are going to be spending money on marketing, traveling, clothes and potential leads/clients. 

I've become obsessed with the idea of using real estate to achieve financial freedom and to fuel my adventure travel lifestyle. 

I have been travelling there frequently and started to look into MF there as well. 

Our ultimate goal is to generate enough passive income to quit our jobs and travel with our kids whenever we want (WITH a nanny of course... that's part of my fantasy). 

I have a cousin who wants to sell his home and travel in an RV with his wife.