One can game political freedom to some extent, but in the absence of certain "political" freedoms, such as freedom of expression, economic freedom can be gamed too. Singapore is a case in point: the government has monopolies on "chokepoints" such as the airport and the Internet (the latter is completely censored) and is a major player in even those parts of the economy that are not dominated by "connected" individuals - for example, 30% of Singapore's population live in government-owned housing.
Although nominal taxes are low, the political class exacts tribute by preferential government treatment of those who "do business" at inflated cost - in effect an "unofficial" tax - with "private enterprises" owned by powerful politicians. For example, the political appointee who runs the government's monopoly airport also owns the "private company" that transports goods from factories to the airport, at exorbitant rates. As the government official in charge of the airport, he decides when goods are shipped by air in and out of the country - and if someone makes the mistake of hiring a different local shipper within Singapore, he finds his goods delayed at the airport.
There is always more than one way to game the stats. And of course Ventura would be the last person on Earth to live in a place where the media and the Internet are censored, as they are in Hong Kong or Singapore.
My bet would be on someplace uncensored and sunny. Bonaire?