I negotiated terms that were a win/win for both parties.

The beach houses in this area are expensive, and may not be the best investment in terms of rental income, but we would really enjoy going there when it's not being rented out.

Here’s an example of bonus depreciation.One way that you can still benefit from a cost segregation study is by utilizing the Short-Term-Rental (STR) strategy on your property.

Somebody said 30 days and everyone followed suit.I was a the Dr last week and the Nurse said Charley Horse.I asked if that was a medical term, which it isn't. 

Advantages/disadvantages about a longer-term lease in this situation?

It has long been a favorite for local investors and in the 6-8 years the word spread and it is a hotbed for many more now.

If the trust mentions the real property, but you never actually transferred ownership of it into the trust, likely the trust terms don't govern it yet. 

I have a particular interest in islands, as my long-term goal is to captain a catamaran and offer tours for snorkeling, sunset cruises, etc.I'm interested in places that offer great ROI without being overly expensive.

Sellers don't want to go down at all even though we try to offer good terms. 

I do very well with the Airbnb income and do not want to turn it into a long-term rental.