Sounds awesome and I want to see it. I wonder what he gives up there compared to the states, in order to have that utopia. Quality of health care, if not cost? Homogenized/consistent public services? Availability of goods/services? Or not much to speak of?Good questions, of course, to see what the cost is. Everything has a cost. From my limited experience, I think all of those things he mentioned are true.
The cost of freedom and harmony is often the quality and ubiquity of services. Most islands don't have reliable quantity and quality of products and services. It is a much more self sufficient environment. Insurance is rare. The islands (or towns) that do have reliable quantity and quality goods and services are correlated strongly with tourists (which usually means white people). Whether the chicken or the egg came first is hard to tell.
In St. Georges, Grenada, where we stayed for 2 weeks, there is a cruise ship dock. St. Georges is the largest town on the island, and the capital, with about 35,000 people. There was more pan-handling than in other towns on the island. Well, there was pan-handling, whereas we didn't experience it anywhere else on that island. Then the cruise ship arrived for a day, and 3,000 white people spilled into the town to spend money. Very different place for 24 hours. Great to be a local business owner, and for taxes to be acquired. But a different feel to the town. Even with all the bustle, it felt... bland. People were just doing business, not saying hi and smelling the roses. When the cruise ship left, the town went back to the way it was before: somewhere between a normal town and a cruise ship town.
The more I reflect on it, I think a single cruise ship dock is a good thing for a country like Grenada. It brings in a ton of money for the people and government, but keeps the damage limited to a fat person's walking distance away from the cruise ship. That money then gets spread around the country. The cruise ship dock attracts small boat cruisers like us, who are willing to pay for reliable quality services. Grenada has a good medical school, and many white people go there for training. There is also a fairly large wealthy ex-pat population in Grenada, so many locals have made good money providing services to them.
To get back to the question, I think yes, in general, the reduction in rules does imply a reduction in services. For me, that is an acceptable tradeoff. A few places, such as Grenada and (I've heard) Australia, seem to have found a middle ground with good services but minimal rules.