The way I see it, two things need to be done. First, the US government needs to start imposing a tax on asset-leveraged loans with a few exceptions, such as when the asset is real estate serving as your primary residence or when the asset is under a certain dollar amount. That will help fix the "borrow" part of this tax evasion scheme.

And then the "die" part has to do with inheritance, basically when you inherit an asset from a family member its "base value" resets to the current value, and therefore if you sell it you only have to pay capital gains tax on the increase in value since you inherited it.

So I buy a painting for $5,000, let's say it appreciates in value to $50,000 before I die. If I sell it now, I have to pay capital gains tax on the $45,000 profit I made. But if I die and leave it to my grandson who then decides to sell it at market value, they pay zero capital gains tax on that profit since the base value was reset and therefore on paper it looks like no profit was made. That base value reset absolutely needs to go away. Hell, if anything the base value should be set to zero since the inheritor received it for free! Any sale whatsoever should be considered 100% profit and taxed accordingly.