Hi @Account Closed - well each island has its own regulations, so I can only speak for O'ahu though I've had clients also look at properties on the other islands. As far as which island is most attractive to investors, that seems to come down to a personal basis. But based on feedback from my clients, many of them decide to invest on O'ahu due to the large number of tourists that visit each year, that O'ahu offers city as well as county life, and that there is a large military population that supports the housing market.
And you are right, property values have increased quite a bit the last couple of years but there are still many people looking to buy STR's on O'ahu so many still think it is worth investing here. Personally, I am very bullish on Hawaii real estate if you plan to hold long term.
If you want to share, what market is your first STR in? How'd you choose that market and what appeals to you about investing in Hawaii?
If I can be of value to you on O'ahu, you are welcome to contact me at any time. I track the STR market very closing here. And if you want referrals to any quality agent on those other island, just let me know.