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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


The 2025 Definitive Guide to Retirement in Portugal: Navigating a New Landscape of Opportunity
Madeira, Portugal Bom dia!!!! If you've been following our "It'll be fun" channel, you know we're all about making the dream of moving...
itllbefunretiremen
Jul 136 min read


What to Expect When Starting a New Life in a Foreign Country
Moving to a new country can be an exciting yet daunting experience. You might be dreaming of beautiful landscapes, unique cultures, and...
itllbefunretiremen
Jul 103 min read
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