Not exactly unscrupulous if he wasn't charging insane rents to himself. His business would have to pay rent or mortgage for office space in any case. And the income his other business would get from the rent is taxable as well. At a certain point, he either has to break a law in an egregious manner and hope he does not get caught, or he has to pay taxes. That's the system we put in place when we start setting up income and corporate taxes to prop up a massive federal government.