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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


Living Off One Social Security Check: A Smart Approach to Financial Freedom
Facing a Chaotic World Together Let’s be honest: the world feels a little upside-down right now. Tariffs are soaring, countries are...
itllbefunretiremen
Apr 105 min read


Living Rich Without Millions—Your Path to Financial Freedom
We've helped 100's of people move abroad and build financial independence. Stop waiting. We should have done this sooner.
itllbefunretiremen
Dec 31, 20245 min read


A Bar, a Garden, and a Leap of Faith Led Us Around the World - Moving Abroad
We moved from Ohio to Chicago and now to Portugal! It's never too late to start a new adventure. Let us show you how to make your dreams com
Leslie
Jul 20, 20243 min read


Navigating the Pitfalls: What Not to Do When Planning to Move Abroad
Moving Abroad What You Need To Know and How To Do It!
itllbefunretiremen
May 8, 20243 min read


The Greatest Gamble: Confronting Risk in Retirement Planning
During a lifelong pursuit of financial security with the goal of a comfortable retirement, we often focus on external factors like market...
itllbefunretiremen
Mar 17, 20243 min read


Spain For Lifetime or How About A 3 Month Stay
Are you dreaming of a retirement filled with sunshine, culture, and a leisurely pace? Look no further than Spain, where the enchanting...
itllbefunretiremen
Feb 23, 20242 min read


Then Vs. Now, Why Did I Wait So Long
Throughout my life, spanning over the last 50 years, a typical day for me consisted of waking up, donning my reliable mechanics uniform,...
itllbefunretiremen
Jul 5, 20233 min read
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