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Two of my favorite quotes on taxes:

The legal right of a taxpayer to decrease the amount of what otherwise would be his taxes, or altogether avoid them, by means which the law permits, cannot be doubted.

George Sutherland, Supreme Court Justice from 1922 to 1938

In my own case the words of such an act as the Income Tax, for example, merely dance before my eyes in a meaningless procession: cross-reference to cross-reference, exception upon exception – couched in abstract terms that offer no handles to seize hold of – leave in my mind only a confused sense of some vitally important, but successfully concealed, purport, which is my duty to extract, but which is within my power, if at all, only after the most inordinate expenditure of time.

Learned Hand, Judge 2nd circuit court of appeals from 1924 to 1961

My take-aways from these two quotes:
1. Tax law is complicated.
2. It is perfectly legal to arrange one's affairs so as to minimize taxes.


PS - One more item to discuss with the lawyers and/or tax advisers. Estate taxes. As two single people, you lose the portability of your exemption between spouses. This is only an issue if your gross estate is over about $5 million. And you'd lose the benefit of an unlimited estate tax exemption on assets left to a spouse.
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