> 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.
How? You would have to prove collusion between them rather than just a normal contractor-type relationship where the contractor does something unsavory entirely of their own volition.
> 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?
Of course. That's exactly what happens in those types of situations. As soon as you hit the 90% rate, the next thing you know the spouse is on the payroll, or the kids, the parents, brothers and sisters, in-laws, cousins, friends of the family etc.
> 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.
Right, which is why you need policies they can't avoid instead of ones like this which they can.
The best way to do this is a UBI funded by a flat tax. The rich can't arbitrage a flat rate and the UBI makes it progressive (meaning net transfer from rich to poor).