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(http://www.irs.gov/Individuals/International-Taxpayers/U.S.-...) -- "Your worldwide income is subject to U.S. income tax, regardless of where you reside."
In case you're unaware, there's also r/IWantOut on Reddit, which is all about this kind of stuff. I'm 'out' (currently Lisbon, previously both Rio long-term and short-term in Medellin) but since I've always tried to get away from native English speakers, in order to have a more 'authentic' experience, I can't say what's good for Americans. Key to me has been language. Get at least intermediate in the one that's spoke…
I'm a Canadian, with a combined admiration and disdain for U.S. society. Actually, that was redundant :). Also, I have dual-Canadian German citizenship and am running a largely telework-friendly business.
I'm building a website that seeks to answer this question and similar questions through user self-reporting of slow travel and expat experiences. http://www.istorical.com A post by a Brit who moved to Prague: http://www.istorical.com/countries/czech-republic/experience... An American's experiences moving to Germany: http://www.istorical.com/cities/berlin/experiences/138 A couple of interesting posts about life in Jap…
Pro's: - Great culture, great food. Groceries fresh and reasonably priced.
- Coming from english, Italian is a relatively easy language to learn and people are happy to speak it with you.
- Pretty good infrastructure. Good train systems to move around the country. Rome has a good subway system.
- Lots of walking/biking in daily life keeps you in shape.
Con's:
- Anything ivolving the government is a beaurcratic nightmare. We applied for student permits in August and didn't get them till after we returned home in January. Never tried it but starting a business is probably a lot of paper work.
- Nothing in the city runs on a schedule Buses, People, any type of meetings. The saying that Mussolini did bad things, but he made the trains run on time definatly makes sense after living there.
- Cost of housing his high, though the outskirts of the city are cheaper.
All in all I loved my time there as an experience, but working there may be a challenge.
One of my favorite links I've ever seen on the subject is this: Top 15 Cheap, Safe and Friendly Countries http://www.kimeshan.com/2013/07/11/cheap-safe-and-friendly-c... Here are the top 15 cheapest, safest and friendliest countries: COUNTRY / RATING 1. Macedonia 0.99 2. Georgia 0.98 3. United Arab Emirates 0.82 4. Morocco 0.80 5. Hong Kong 0.75 6. Montenegro 0.71 7. Malta 0.68 8. Taiwan 0.67 9. Ethiopia 0.63 10. Tha…
Also, cheap only matters if you plan to continue to work remotely. If you eventually want to work locally to be near colleagues, Ethiopian prices may be low, but Ethiopian wages are also.
Given that he has children, I'd also think that the education system is an important factor.
If you are young, embrace the opportunity to learn a second language. Take a course before you leave, study your new language thoroughly, and bask in the joy of being accepted in a rich new culture. The culmination is when you can understand their jokes. The motivation is to bargain successfully in the marketplace (eg. Latin America) and not get taken advantage of. I lived in Peru/Bolivia in 1968-69, taught high scho…
The trick, IMHO, is to have some local knowledge of what's what and then to be firm in everything (and not afraid to say 'no').
If the phrase "you can't bullshit a bullshiter" is taken into consideration, the appearance of having adopted such a stance makes one pretty much immune from being taken advantage of. For anyone considering LatAm, just let people know they can't pull the wool over your eyes (no pun about llamas intended).
You are asking a lot of questions but it would help people to understand what you are looking for (or what you are moving away from). If you are looking for almost USA that is not USA, then Canada. If you are looking for a good climate outside of USA then Australia. Or France, or Italy, but then you will need to learn the language. If you are looking for low expenses, then India, Thailand, or Vietnam. If you are look…
I saw a lot of American expats in Chiang Mai, Thailand. It's much more laid back than Bangkok or the beach cities, and it's gorgeous up there. They seemed to be having a great time.
Watch out for the whole double taxation issue. You will need to pay taxes to the US (there's a certain income threshold if I remember correctly, but you'd likely surpass it). If you wind up taking permanent residency, you may need to renounce your US citizenship to stop having to owe taxes Stateside. ( http://www.irs.gov/Individuals/International-Taxpayers/U.S.-... ) -- "Your worldwide income is subject to U.S. incom…