Define your investment goals, familiarize yourself with related terms, evaluate your financial situation, begin small, investigate markets, establish investment standards, cultivate professional connections, carry out exhaustive due diligence, investigate funding alternatives, and determine whether to manage the property on your own or by hiring a property management company.Decide what you want to achieve—stable cash flow, long-term growth, tax advantages, or all of these—and dedicate some time to learning about them by reading books, using the internet, taking classes, and attending seminars.

And frankly, you have similar or nicer beaches in well-established tourist destinations much closer so why would they bother?

Since we established that listings cannot be transferred they cannot directly add to the overall real estate value of a property.

We are transitioning into the US Market, and looking to partner with established and experienced developers. 

Small unit, newer renter I will take personal references from neighbors etc. combined with an established job in the area or a new job with a strong employer in the area.

It is a lot to juggle. 

There is a lot to know and you don't want to introduce too much new risk.

These places will be more expensive, for a reason.Now I do think that there is some opportunity in certain areas of upstate NY for short term rentals, however upstate NY is not a well established travel destination so your occupancy will probably be low and highly seasonal but this method is viable.

FF is just one source and good for establishing a baseline of sorts, but I agree with you that it's going to be beneficial to market on other sites, including the OTAs.

I was wondering what everyone's experience with establishing a legal entity for REI has been like, and when do you recommend a person to do so?