My taxes for 2025 were exciting due to multiple characterizations of the same contracting income (US sole prop. before departure, PT sole proprietor for 4-5 months, PT single-owner LDA (LLC) for December), and the need to submit both business and personal returns in Portugal. Under the circumstances I paid a substantial fee to a company in Lisboa specializing in expat tax issues, who has a US partner they collaborate with to sync up the returns with respect to the foreign tax credit and the like. It is a very different scenario than the majority of US residents here, who are retirees.

So far, I'm satisfied with the tax consultants. They suggested I could characterize the PT LDA income as foreign-sourced, which meant that I had quite low PT taxes for the year, and the tax authority just accepted my return on that basis. Hopefully that means they will not contest the characterization. The US return has been deferred pending completion of the PT return and I hope it can all be wrapped up soon. I really can't imagine trying to do this myself, even if I were fluent in Portuguese - which I am very far from.

2026 will be a lot different, with all work income flowing through the LDA but the Portuguese "NHR 2.0" favorable tax regime in effect. Really no idea how that will work out yet, but given that most of my income would otherwise be in about a 51% + social security tax bracket, hopefully it will not be too bad. My hope is that my US tax liability will largely be wiped out by the higher PT rates, as I would far rather pay taxes to my new home (but not 51% marginal rates).