I find this kind of high-level thinking about hierarchy and conflict in society to be pretty silly.

It's true that there's always some insight to be gained by bringing ideas from different times and places together, but in this case, the comparison is completely arbitrary. Conflict and oppression has been going on for all of human history, and in theory, all of that combined knowledge could be put to use in helping resolving present problems.

Why compare the Iraq war to the American civil rights movement when you could equally well bring up the French Revolution, the Tuareg Rebellion, or the War against Gallus?

because those are both traditional and obvious comparisons; this one is neither - not to mention it's good to discuss given the times

This comparison doesn't seem particularly valid.

Insurgencies operate by leveraging small-scale, decentralized groups against a large, slow-moving beaurocracy. They succeed by operating faster than the beaurocracy (inside their OODA loops), leveraging the environment to their advantage and attacking critical points of failure. They're difficult to fight against because of their speed and the fact that they don't readily present targets to be attacked.

Granted, the Civil rights movement was largely grass-roots, but it's not clear to me why a comparison to an insurgency is apt.

by this definition most elections could be classified as insurgencies as well

The founding fathers used the word 'revolution' rather than 'insurgency,' but yes, that's sort of the point. It's better to have a structured, nonviolent way of overturning the current social order, as the alternative ways are rather messy and ill-thought-out.