I have family that owns several properties on Maui, but they went the more traditional route of buying the condos and then renting them out on VRBO. The issue with that is the one you mentioned, it is capital intensive, and VRBO and AirBnB carry with it regulatory risk. I have looked at buying property on one of the islands but it is difficult to make the numbers work at the moment. The ideal situation is to buy into a undervalued market and have those investments produce enough cash flow to get a toe hold into the Hawaii'n market. We are seeing people have success with buying small commercial apartment buildings in smaller cities (ie Omaha instead of Seattle or Nashville 5 years ago instead of San Francisco or Chicago). The capitalization rate you would find in Hawaii or the West Coast almost necessitates capital appreciate above inflation to make them profitable and that introduces quite a bit of risk. I have definitely seen people get burned here on the coast.