I think you understate the extent to which one can use a tax-deductible non-profit organization to benefit oneself. For example selective private schools are a

I think you understate the extent to which one can use a tax-deductible non-profit organization to benefit oneself. For example selective private schools are all (at least in my area) not-for-profit organizations to which contributions are tax-deductible. So you "give" to these organizations and essentially pay for private school from pre-tax income. There are even country clubs that are non-profits. I think the only thing that really prevents these organizations from being formed are if they have documented written policies of racial discrimination, in which case the IRS will go after them eventually.