It's not a false dichotomy, it's actually what happens because the newly rich are often earning their new riches in a way that is not easily hidden away in any of the myriad of legal structures that can hide income permanently from the high tax countries. The new guys will get their wealth eaten by your proposed policies but the old wealth will not, calcifying the system.

It is the wrong question about Jim Walton because it only matters if walmart is still the obvious oligopoly abuser it is. There is a huge difference between someone who managed to get big enough to abuse market power in one space and collected monopoly rents to amass a large fortune (The waltons, bill gates, etc.) and the guys who appear to be excellent managers and have grown massively society improving businesses in disparate industries (currently only Elon comes to mind, I am sure there are other but they are rare enough and/or have stuck to a single business that they grew large enough to extract excess profits that I can't think of any other semi proven names). The good managers you want to be as rich as possible because they are deploying that cash well, the other guys not so much. This translates into much more concern about the children of the super rich (which is correct) but to which you are trying to solve with an inheritance tax, which will just make things worse and slow growth. It's far better to break up the monopolies/oligopolies/regulate away the most obvious abusive contracting and let time do it's thing to get the junk offspring back to normal wealth levels.

You don't get it. Reporting requirements are quite invasive now and they aren't working. The level they will have to get to to actually make an inheritance tax work is a place that is far too much power for the government to have and won't end well (because that level of power has never ended well in the hands of the government). You are trying to solve a questionable problem (billionaires) by feeding an obvious, terrible, and literally deadly problem with massive historical precedent (government power).

If Walmart is broken up and Jim Walton is forced to divest, he will invest his money elsewhere and still own the means of production (capital) just in other companies.

It doesn’t solve the underlying issue of wealth distribution.

Of course it will, just not on a very quick (and destructive) timeline. He loses a monopoly abusing company and its excess profits which fed inflated salary and stock compensation for him personally and is instead left with taking the equivalent of the S&P 500 return or trying his hand at actually being a good manager and growing a company from small to large again or investing in early stage private stuff and experiencing the huge risk of that. If he's actually a good manager/ entrepreneur he can still grow his wealth starting something new, if he's not then he, or his kids, or his grand kids will eventually put enough of the wealth into failed company ideas, up their nose, in their veins, down their throats, into bad real estate, etc. that they cease being billionaires and have to get real jobs. This is the classic way wealth was dissipated. It's non violent, slow, but effective. most importantly it doesn't ruin the calculus on whether someone should strive to be a great entrepreneur or just keep their head down because they can be sure the government will steal it if they succeed.

I think we should aim to do better than fixing it across a 200-300 year timeline.

It’s not particularly ambitious.