Is the often stated US goal of bringing democracy to other countries a wise pursuit, i mean or does it depend on how you go about bringing this change, Iraq is an example here? The US has supported the overthrow of legitimately elected governments, Chile 1973, Guatemala 1954, Iran 1953, by some accounts Nicaragua after their 1984 election, why support dictatorship and what do we stand to gain from this.
I think it is often not a valid pursuit, there are times where other types of government may be more suited to the region or country in question.
It is also rather easy to look at our own model of democracy and suggest that we ought to be re-considering how effective it is and whether we ought to be the ones spreading it to the world given our own issues.
Democracy has a high sounding connotation to anyone American; however in the last analysis, democracy is a purely Western concept. It originated with the Greeks, made its way into Western Europe, and found its figurative home in the United States.
Over the last century or so, however, Democracy has taken on almost missionary elements. Americans feel a duty to carry it to other areas, just as Christians feel a duty to spread their religion to the "heathens." Democracy is a fine fit for Western culture; but some parts of the world are not western in their culture, religion, or politics. To imply that they MUST accept democracy because it is superior bears a striking similarity to the idea that western culture is superior to all others.
I am old enough to remember when the World History taught in schools was western civilization. The implicit belief was that all other cultures were uncivilized. At times, I think we are guilty of the same assumption about democracy as compared to other forms of government.
The US will always support whatever regime seems the most stable, and whichever one has matching interests. In general, we do not favor dictators, but if they promote stability in the country we might ally with them. The US, on principle, does not support any regime that violates human rights.
The idea behind supporting dictatorships at times is that democracies can support people and ideas that we don't like. Therefore, while democracy might be the "moral" choice, it might be better for the US to support dictatorships (we tend to think).
Look, for example, at Egypt. We supported the Mubarak regime even though it was oppressive. We did so because A) Mubarak was friendly towards Israel and we support Israel, which needs all the friends it can get in the Arab world and B) we were afraid (and still are) that a democratic will become an Islamist state. We're afraid that democratic Egypt will support Al Qaeda or at least give support to people like Hamas (another example of a democratic election backfiring on us) and hurt Israel and our general goals in the region.
So, we tend to support dictators when we think their policies will be better for us than the policies that would be chosen by democratically elected leaders.