> In 2015, he was denied a visa to reenter the United States by the U.S. Embassy in Barbados, which claimed that he had not sufficiently proven ties outside of the United States that would motivate him to leave at the end of his visit, causing fears he might become an illegal immigrant.[8][7][9] Later in the same year his visa was approved by the U.S. Embassy in Tokyo, and he visited the United States in June 2016 to speak at a conference in Denver, Colorado.[10][6]
Its a fun thought experiment for sure but ultimately if you're at the level of wealth that running from the taxman gets you huge gains, either you have other problems (like being some sort of druglord) or you have enough money to also just pay taxes
But it seems that a lot of people disagree. Either you and I are massively underestimating the benefits of tax avoidance, or these people have some sort of knee-jerk reaction to the very concept of taxation that makes them try to avoid taxes even if it involves a lot of hassle. The latter would not be surprising for a diehard libertarian.