Forms of liberty worth having

Been having a very fruitful debate with a conservative on the discussion board for my Microeconomics class.

I'm seldom able to finding conservatives who actually take the time to truly engage and debate issues indepth, and it truly is enjoyable when I do as I actually learn a lot in the process both about the reasons behind some of the positions I disagree with as well as getting a better understanding of my own positions and flaws in those positions that I can improve upon.

One thread I've been thinking through is the importance of definitions of liberty.  

Definitions of liberty that lack the right of self-government, of choosing ones leaders, isn't a form of liberty worth having.  I think I see a tendency within right-libertarians and conservatives to champion liberty that either openly denies self-government as a right that all have, or at the very least support policies that imply a denial of the right to self government as an unstated premise.

When you lack a heuristic device to deal with disagreements about what a policy should be you end up either imposing a subjective version of coerced/uncoerced policy.

Is social security a nanny state system that coerces people, against their will, to put money into retirement funds that individuals would rather invest on their own.***  Or is social security a social program that the demo's voted on and supports.  The self-governed should have a right to set up a safety net no?

I look at Libertarians like Jason Pye and the crew over at United Liberty as examples of people that claim liberty at the forefront of their belief system but appear to lack the needed heuristic to resolve the self-government impasse. 

***I think its a fallacy to claim that social security is a retirement fund--its a safety net of last resort which protects society from having to deal with the social costs/externalities of large masses of impoverished seniors burdening the economy.