Thanks for weighing in. I have met with a Portuguese Tax Attorney and it is straight forward. There is a defined path to becoming a Tax Resident in Portugal. Anything happening before that day, is not taxable by Portugal. It was suggested to me by a Portuguese Tax Attorney (and an American Tax Attorney) that I take the Capital Gains tax pain in the US now. I wanted to make sure that my reasoning on keeping my taxable income under the threshold of $583,750 + the standard deduction of $29,200 thereby securing the 15% Capital Gains Tax Rate was sound.
Portugal has a Tax Treaty with the US whereby I avoid double taxation. I am part of the Non Habitual Resident tax scheme in Portugal, which means I pay a flat 10% tax on income (as I will be paying more than that in the US I probably won't be paying anything in Portugal). Capital gains on Real Estate are taxed at 0% BUT Capital Gains on investments are taxed at 27%
