Personally i wouldn't have an issue if he paid little or no tax, provided it was done within the confines of the tax laws as they stand as the time of submission. All good business men / accountants would do this to the best of there ability. I mean why pay more than you need to. I know in my businesses my accountants both in the UK and USA work very hard to legally minimize my tax burden.
The bigger issue would be where his money comes from where he borrows money from and his total assets compared to his assets declared on his insurance and loans. This is where he would have issues ?
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