@Jeff Wagner I'm going to St Thomas in two weeks on vacation.

I also have a primary residence with nearly a JUMBO loan at a high interest rate and I own a vacation place in cash (small trailer not worth much money but i also own the land) in a different state that I pay RE taxes on. 

I would definitely, 100%, get a good level of liability insurance if you're going to have it as a rental, and even more if it will be a STR, where people will be on vacation and probably partying.

Another investor's goal is income, so they save and save until they can buy one high-end door (say a vacation STR) and that makes $3,000/month cash flow.

I would have to think that the USVI are a great place to visit for vacation, but you are going to be competing with the inclusive resorts.

If your going into it as just a way to make a buck, with no real passion, then every “problem” will be overwhelming, you’ll be “clock watching” waiting to take a vacation, and dealing with “tenants, toilets and banks” will be a tedious chore.  

(Max vacated rents - your monthly mortgage payment) = +/- net cashflow. 

I am looking to purchase a vacation home in the Phoenix AZ market. 

But increasing stories like this one, are ruining family vacations/stays! 

I did vacation in OBX once and I believe it was in Hatteras if memory services me right.