@Alton P.,
It looks like you have gotten a lot of different views and suggestions from everyone. A lot of them would probably work out great, but ultimately you need to do what works for you.
I am a property manager here on the Big Island in Kona. We manage a large portfolio of homes(120+), and have managed units from $1,000/month to $30,000/night. As you have seen from others, each island has its own rules and regulations. It is somewhat imperative to have someone in the market that knows and keeps up with all of the rule changes if you are going to invest out here. There is a bill currently in legislation in Hawaii County that is changing several items that affect rentals. They are on the 7th draft of it.
Appreciation is the obvious play out here on the Big Island. There are very few properties that cash flow if they were bought today, but that doesn't mean that they don't exist. The most common ways(and maybe only ways currently) to cash flow here are large, high priced & high performing STVR's, or multi-family properties. One of the STVR properties that we manage is actually on the market at $5,900,000 currently. The property usually averages about $400,000/year in bookings. Combine that with appreciation and it could be a viable option.
I also know of two different multi family properties right near the heart of Kailua Kona that are on the market as well. One is a 10-unit complex, listed at $3,000,000, and the other is a 9-unit complex, listed at $2,700,000. They are actually side by side buildings. They are underperforming rent-wise at the moment, so would be a solid value-add play if you had the capital.
Let me know if you have any questions on the Kona market and I would be happy to help out if I can.