This paper discusses countries along the dimensions of democracy vs. autocracy, income equality vs. inequality, and economic rent-extraction vs. creation and compares them in a regional context. Transitions within those qualitative characteristics are generally scarce. When occurring, they are limited to one aspect only. Transitions towards more democracy, income equality, and productive economic activity are most likely when relative equality is already given. Contrary to the general redistribution hypothesis of democratisation, this suggests that successful democratisation stems from initial income equality; it is not democratisation that leads to more income equality. Rising income inequality is identified as the greatest threat to the sustainability of favorable socioeconomic and political developments. Copyright © 2010 John Wiley & Sons, Ltd.