This is really interesting as I haven't heard anyone make such a case for Puerto Rico before. And are you enjoying living there? If you don't mind me asking, do you earn all of your income online or did you also start some sort of business in Puerto Rico? I'm mainly interested in that because I write for International Living Magazine and I always have an ear out for destinations North Americans have moved and have discovered enjoyable ways to earn a living too. My husband and I currently live in Costa Rica. Crazy that the US I believe is the only, (or one of the only) countries that requires you to pay income tax even if you're permanently residing elsewhere. While we don't get to take advantage of quite the break you've outlined here, we have been able to take advantage of the foreign earned income exclusion which has been really nice. Maybe if its something you have some expertise on, an idea for another post sometime! I always find when I tell friends and family about this, they're usually clueless as to the fact that such a thing even exists - one of the many benefits we've found to living abroad. The beach and year-round sunshine don't hurt either :) This was a great post!