I think you’ll find some good advice here and elsewhere on the web on how to succeed in doing this. In general, I think you can be very successful in having a vacation rental “pay for itself” but the biggest mistake I see people making is trying to do everything themselves! This can tank you early and often, especially if you are new to managing in the vacation rental industry. I would suggest using a property management company that has the proven ability to increase booking rates and manage in this modern age. This means they have to be fluent in managing bookings and guest interactions on all the major online booking sites like Airbnb, VRBO, etc. If you were on the west coast I would suggest Pillow, as they are the best option in this area, but I know they’re not on the US Virgin Islands…yet. I would look at their offerings and try to find a company similar in your desired area. Yes, you may have to pay a little more upfront but I promise you it will be worth it and will make sure your vacation rental “pays for itself” in the long run. Hope that helps!