I appreciate your willingness to elaborate on your points in detail. And that you focus on asking questions rather than proselytizing.

>How does the imposition of obligations to "society" through an involuntary social contract differ from slavery itself?

There are a few distinctions that I don't think your analogy captures. It would be an apt analogy if 1) slaves got a chance to vote out their master at reasonable intervals and 2) you have the ability to go to different plantations.

You could go to another society if they are willing to have you. But then you'll be governed by their rules. The only way out of this is to find a patch of land outside every other society's jurisdiction. So yes, we have to balance our own interests with that of the group we associate with. You've probably heard this before, but I'll take a chance at outlining a hypothetical: Assume you're on your condo balcony on the 20th floor but trip and fall. Luckily, the person directly below you on the 19th floor has installed a flag pole that you grab ahold of and you can slowly start walking yourself back hand-over-hand. But hearing the commotion, the neighbor comes out and proclaims you must get your hands off their flagpole. There's really only two possibilities if you believe in the sanctity of personal property rights: 1) you ignore your neighbors commands and walk yourself back to safety, meaning you are immoral or 2) You let go and plunge to your moral death.

I think almost everyone picks scenario #1 because we implicitly understand that certain ideas like personal property rights are guiding principles and not dogmas. Meaning we understand they are not absolutes and can be modified when there is enough at stake. We may debate about what constitutes "enough at stake", but they are not meant to be a suicide pact.

>This seems to be an accurate description of the real situation though, doesn't it?

This may be getting to the heart of where we disagree. I don't think it's a particularly good representation of the real situation, mostly because society is too complex.

I think there's a reason that most society's evolved toward nation-States. There are certain economies of scale that need to occur as society gets more complex. (This isn't to say it's the end-state of the way societies will be governed, either.) At a certain point, we no longer have the bandwidth to make all the decisions necessary for a completely individual decisions to truly be cooperative. We just didn't evolve to operate in systems that include millions of direct and indirect interactions. So we develop systems to mediate these interactions, like representative democracies and home owners associations and all kinds of other groups. And with this comes balancing some of those individual principles with the needs of the groups. I also don't think I'd agree on your assumption that safety and flourishing are zero sum; can you elaborate on what you mean? I think the libertarian principles are romantic notions that fits well under the Jeffersonian ideal of a yeoman farmer, but largely incompatible with the complexity of modernity. To that extent, I'm not 100% convinced that going to the extreme would increase flourishing writ large.

>What happens to individuals who lack merit in a meritocracy?

I don't think they flourish as well as meritorious individuals but I think a moral society has an obligation to provide some baseline level of quality of life. But this question is a bit of a digression from the original topic regarding whether or not society is structured to actually identify those with the most merit.