I am always amazed at the proof you present that humans love to design complex systems....just because.
One would think we could stop...but the "arms race" for even more complex systems to either "trade/hide/obscure" continues unabated.
This reminds me of reading a book, maybe it was called "The Fair Tax Book" and it mentioned how a significant amount of business profits go into managing the complex accounting necessary for "legally" reducing taxes, much as you alluded to, as this circus act is a very complex system.
The book promoted the idea of changing the current Income Tax to a national Sales Tax, collected at the cash register and managed by the states. (which would require passing a constitutional amendment to implement)
This scheme would reduce the burden upon businesses committing significant resources to tax management, make it nearly impossible for anyone to evade taxation by any means. When you buy something from a business, you pay the tax. Which would be collected at state level and forwarded to the US/DC folks.
This would drastically simplify collection and processing of the tax by eliminating the byzantine maze of regulations and staff currently employed to support the existing scheme. The filing of a "tax return" would become an oddity of the past. As would the prosecution, fines, etc. people have to deal with as it is.
The profits saved could be used to increase benefits for employees and/or reduce prices to their customers. This would be a staggeringly significant amount of costs for non-productive tax management processes that could be eliminated.
Of course, this would never work. There are too many influential people whose careers on both sides of the system would be made redundant. They would have to find more productive ways to apply their finely-honed talents that would no longer be needed.
However, Tony Seba, Elon, and others see a world of abundance on the horizon. One established through the development of reduced energy costs and the application of robotic and AI based labor becoming dominant. Taking a significant amount of cost out of the system in ways that don't require getting those depending upon the tax system for employment to buy in.
This scenario would achieve essentially the same result as that idea outlined in the book, because the lower costs of energy and labor will reduce the impact of taxes simply due to there being less money in play. This abundance would also support a workable version of Universal Basic Income assuring reduced or total elimination of poverty concerns.
This convergence toward abundance is happening now, and because it will be based in reduced costs across the board it will be embraced and adopted as a matter of course in order to remain competitive in the business environment.
HODL