Is The Tax On Inflation Tax Really A Regressive Tax?

[Bryan Hancock]

Bear With Me...And Please Forgive My Tax Maze Ignorance

My understanding is that the basis of investments is stepped up at the death of individuals who execute transactions in a tax-efficient manner. For instance, taking a loan out (i.e. HELOC) on a property to monetize instead of selling and incurring a capital gain would allow for a stepped-up basis at death and a smaller tax liability. I am sure there are hundreds of other games like this that can be played as well.

So the question is whether or not this sort of tax is really regressive using the following logic:

1. People with money can hire advisors that would likely know about these games
2. People without money cannot
3. It seems logical that this would make the tax regressive past some breakpoint

If the government continues to deflate the currency going forward and the tax on inflation tax becomes more common will we see even more "revenue" transferred to the government coffers from those under said affluence barrier? Is this really a regressive tax?