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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 156 min read


Social Security for US Expats: Will the Rules Change? (2025)
Your Social Security Abroad: The Rules, The Rumors, and What You Can Actually Control.
Let's talk about the single biggest financial question that lands in our inbox. It’s a one-two punch of worry that can stop a beautiful dream in its tracks. This is a huge deal. Your benefits are the financial bedrock of your retirement, and uncertainty around them is paralyzing. So, let’s tackle both parts of this fear head-on, and then talk about the only mindset that will actually get yo
itllbefunretiremen
Aug 34 min read


Buying a House in Portugal with a Mortgage? Our Unfiltered Guide
Dreaming of buying a home in Portugal but need a mortgage? It's a minefield. Sellers want cash and won't wait for bank approvals. We're Alan & Leslie from It'll Be Fun, and we've cracked the code. Our guide gives you the real scoop on how to navigate Portugal's hot market, beat cash buyers, and secure your dream home without losing your mind (or your deposit!). Learn our strategy and get the expert team you need.
itllbefunretiremen
Jul 96 min read


Moving Overseas - Takes More Than You Think
Thinking of moving to Portugal from the U.S.? Don’t wing it. From visa types (like the D7 or Digital Nomad visa) to real income requirements and unexpected costs, we break down what it really takes to start a new life abroad. This isn’t a vacation—it’s a life reset. Get clear, get organized, and do it right the first time. Bonus: use our 30% off code for the Ultimate Moving Abroad Program!
itllbefunretiremen
May 104 min read
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