I think you're presuming the loophole here a bit too quickly. It shouldnt be difficult to determine when it is that a wealthy person hired a less wealthy person to do the unsavory thing in order to exploit the lower fine.

More to the point brought up about Finland's lower wealth inequality: yeah, that should be what we're shooting for. Say we return to a robust progressive income tax system where if you make over say, 10 million dollars a year, you get taxed 90%. The arbitrage loophole doesnt work because, what, are you going to split up your 10M/Year income between 20 different less wealthy people and have them spend your money for you in order to avoid the tax?

What am I saying, of course the rich would find a way to skirt taxes. It's like, their whole shtick. I loathe the whole "Of course I'll do every shady, up to and including illegal things, to pay less taxes because if theres a loophole I want to exploit it". No, in fact you are acting being an anti-social cretin who neglects to give back to the society that produced the material conditions that allows for your wealth.