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Navigating the Politics of Paradise: Where Does Your US Political Mindset Fit in Southern Europe?
Alan enjoying life The dream of packing up a life in the US to retire or build a digital nomad career under the suns of Southern Europe is a powerful one. Whether it’s the rugged Atlantic coastline of Portugal, the historic hills of Rome, or an island sanctuary in Greece, the aesthetic appeal is undeniable. But when Americans make the move, they often bring along a mental map of politics shaped by a strict Democratic-versus-Republican, red-and-blue landscape. Applying that bi
itllbefunretiremen
Jul 105 min read


The Ultimate 2026 Move Abroad Map: Where We’d Look If We Started Today
Chateau de Chantilly France
itllbefunretiremen
May 299 min read


The Long Game: Why We're Sticking with Portugal (Even with the 10-Year Rule)
Why Living In Portugal Is Worth It. Even with all the political issues, policy changes and high taxes. There is something to be siad for this country. Come join us to see how we have built our It'll Be Fun Life.
itllbefunretiremen
Dec 12, 20258 min read


Portugal's Citizenship Changes: What You Need to Know - UPDATED
Father and son in palermo Italy
itllbefunretiremen
Oct 26, 20255 min read


U.S. Expat Retirement in Europe: A Looming Tax Storm?
How Much Is too Much to Pay In Taxes? For the millions of Americans retired or retiring across Europe, financial planning has long been a balancing act between local tax laws and the unique demands of the U.S. tax system. Favorable regimes, like Portugal's recently ended Non-Habitual Resident (NHR) program, have offered years of stability and significant savings.
itllbefunretiremen
Sep 12, 20256 min read


Our Portuguese Dream Condo Became a Full-Time Airbnb: The Legal Loophole We Never Saw Coming
We thought Portugal's new housing laws protected our condo from short-term rentals. We were wrong. We understood the rules but missed the math. A legal loophole allowed wealthy investors to gain a majority in our small building, legally turning our home into a hotel. This is our cautionary tale so you can avoid our costly mistake and understand the risks before you buy.
itllbefunretiremen
Aug 15, 20256 min read
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