I left the US for New Zealand in 2008. My wife and I always wanted to live overseas. It was during the financial crisis, she worked for a major financial firm, and her boss told her she may want to start sending out resumes, so we thought we'd give it a try. Also, both of us have always had a conflicted relationship with US culture. We applied for permanent residence visas and she was able to get a job in Wellington. I've always been a freelancer, so it was hard to land a job while still living in the US, but was able to find work about 4 months after we arrived.
We applied for permanent residency because we thought we'd be there long term, but after a few years we realized it wasn't for us. A few of the reasons we left New Zealand were xenophobia, lack of skills in the work place, terrible housing, total lack of art, puke everywhere in the streets, it's a horrible place to be outside, if you're not getting majorly sunburned on a 60 degree cloudy day because there's no ozone layer, you're getting bit up by sand flies, and a little island fever to boot. I still really like a lot about the government agencies in NZ, and we actually had decent health care.
We moved from NZ to France. We both really liked it there. We spent three months in Nice brushing up on our French and getting some much needed sun, then moved to Paris, where we spent 9 months. We met great people in France, loved the culture and the cities, but we were only able to get student visas(that we were too old for, but they gave them too us anyway), which only allowed us to work part time. It became clear that my wife and I would have to get divorced and marry French nationals to get any sort of proper visa, so after a great year we packed up again and headed back to Brooklyn.
Right now we're looking into moving to Portugal through one of their real estate or investment visa schemes. It will probably take a few years to put something together there though. Why? Portugal is kind of out of the way and nobody seems to mention it much, lots of cheap property, and we both really enjoyed it when we visited a few years ago.