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What are the downsides that prevent more people from working in high-income countries, and then retiring in low-income (and cost of living) ones?
Political instability and general inability of the government to control crime, economomy, or even remain in existence, would be my greatest worry.  I wouldn't want my bank account to randomly disappear, criminals to come take my stuff and/or life by force because nobody is going to stop them, or a hoarde of revolutionaries appearing at my door telling me "get lost, the times they are a-changin". On a whim, I tried to compare instability to cost of living.  I used lowest monthly disposable income as my correlation to cost of living and the Fragile State index to measure instability.  I picked the 55 lowest to get the countries with $500.00 (usd) and lower in monthly income.   Those countries average out to 83.42 on the Fragile State index, which would be in the "Very High Warning" range and includes 18 countries in the "Alert", "High Alert", or "Very High Alert" status. Obviously, there is some subjectivity in an attempt to measure something in as broad a term as "fragile state", but it illustrates it's point well enough.  Sources: http://en.wikipedia.org/wiki/List_of_countries_by_Fragile_States_Index http://www.nationmaster.com/country-info/stats/Cost-of-living/Average-monthly-disposable-salary/After-tax