Benevolent dictatorships are fine as long as you agree with the king/laird/CEO/ whatever.
Fall out with him and you'll lose your house, your job, and all those related to you might suffer. Rich people running islands is not a great long term plan. Ask the population of Eigg in Scotland, for example. All good until your nice rich person gets bored with his toy and neglects local services that people need, or sells it to a Bad Rich Person, etc.
I would have though US citizens, of all the places in the world, would have a historical perspective on what happens when uncaring kings run your country, and what the poor but honest citizens should do to resolve the lack of decision making power.
Very curious. Of course Ellison might be a lovely chap and improve the situation - it sounds like people do need improved services... but one man owning an island and having no accountability on his decision making power over people's homes and jobs, this makes me nervous... it's not like the people living here can change employers or move down the road if they are unhappy, it's an island. I'd be interested to hear his thoughts about the democratic processes, how the local people have the option to veto his decisions if they disagree, and so forth.
If he's really in it for the long term, wouldn't it make more sense to go for independence from the USA and ask the people to elect him as their President?