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Trying to establish a set of rules for what counts as a business expense and what doesn't for the infinite number of changing industries is a futile task. It also creates weird situations like Apple harboring cash outside the USA.

We should get rid of the corporate tax rate and tax money when it comes out of corporations to real people (dividends, buybacks, etc) at a revenue neutral rate. Would make things a lot cleaner

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All this means is that large net-worth individuals will increase the practice of keeping money within a corporate structure and using that for as many expenses as possible.

Through what mechanism can a large net worth individual get a company like Apple to buy things for them? They're not the only shareholder

This is also possible to do today and when it happens the SEC investigates whether a $100M painting for the CEO's office was an appropriate expenditure of other shareholders money. The tax policy doesn't have a bearing on this type of fraud

letters of credit or equivalent, heck there are whole circuits already that work like that, they move around credits at neutral exchange rates so they end up financially as exchanging debts, like sardex.

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