After much though on the issue I have come to one conclusion on the whether guerilla is the answer to the problem of defense in a free society: clearly not!
Guerrilla is useless for a free society. The reason is simple. In a normal war, the frontline is the line where the division of labor ends. If we forget about the operetta wars of the civilized ages, it becomes clear that no trade can flow through a front line for long, whether formal embargos are in place or not.
The principle of guerilla is to turn the whole country into a frontline, thus the division of labor through and through must end! The first principle of guerrilla is that it can only be waged in a world of self-sufficient farmers. The same goes for civil war, which is just a war where both sides employ guerilla tactics.
The Israelis in 1948 where a nation of farmers and could fight guerrilla style. The Albanians in Kosovo 10 years ago where a nation of farmers and could go guerilla. Vietnam was a nation of farmers. Afghanistan has always been a nation of self-sufficient farmers and herders. There just isn’t one example where a successful and intense guerilla action has been fought by a stratified society.
Thus it becomes clear, that should a free society be invaded, it’s only recourse would be to destroy it own prosperity by engaging in guerrilla. It is not puzzling then, that many a people in history have chosen subjugation, rather that the eradication of their cities (and thus of their culture) by going guerrilla. Until 1945 there just wasn’t any way for a stratified society to defend itself save for regular armies and geographic features.