If you're rich enough, you can fly your family and friends out to any tropical paradise whenever you want. No need for you to visit the US unless you have a strong emotional attachment to some specific location.
if you are rich enough you can also just pay taxes and keep a passport that allows visafree travel mostly anywhere and not have to force people to fly to a different country to see you.
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
Sure, if I had to choose between maintaining a complicated tax avoidance scheme for the rest of my life and just paying taxes, I would probably just pay my taxes and sleep easy.
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.
If you have enough money to pay a tax-hiding-specialist, then it's no longer a hassle, it's just another person you pay to take care of your stuff - perhaps analogous to a nanny or butler.
