A long, disconnected, and incomplete rant:
There are two different sorts of political disagreement among non-idiots -- disagreements about the likely consequences of policies, and disagreements about values. In practice, people tend to conflate these, esp. where there isn't an academic consensus, and adopt narratives that suggest that policies they disagree with would be disastrous regardless of values. This is usually, though not always, dishonest; few problems can be solved by dominance reasoning.
I'd describe myself as a left-wing individualist; I'm antagonistic in the abstract to most forms of communitarianism, unions, small-business-worship, homeschooling, extended families, nationalism, ethnic pride, segregation, etc. (And yes, from my perspective left-wing and right-wing communitarianism are similar phenomena.) On the other hand, I believe a fair bit of the negative communitarian case against modernity and modern liberalism: I'm not convinced that progress makes people happier; I agree with Naomi Klein (whom on the whole I dislike) that corporate interests corrupt politics, and that either politics must be insulated from big business or big business must somehow be shrunk (I'd prefer the former); I buy the conservative belief that diversity and urbanization spoils the sense of community and the real benefits that come with it (though I'd say, if so then fuck the sense of community). Etc.
I'm unsympathetic toward libertarianism largely because I don't believe libertarian arguments. The value system, on the whole, I'm not that antagonistic towards. I'm in favor of wide personal freedoms, a moderately strong system of property rights -- that is, I would like property rights to be strong enough that they are predictable, which is a pretty powerful constraint -- and flexible employment. (On the other hand, flexible employment includes people with preexisting conditions; the current system, where some people simply can't afford to lose their jobs, strikes me as intensely wrong. Similarly, I think that people in general ought to have the right to free speech de facto and not just de jure; one shouldn't be liable to starve for protesting.) Lateral mobility seems at least as important as upward mobility, esp. assuming long lives and rapid technological change; I'm in favor of a reasonably strong safety net that allows people to change jobs in mid-career. And I just don't think any of this is possible without big government and high taxes. I am quite strongly against outsourcing the safety net to families, charities, etc. because they're bound to be discriminatory in ways I disapprove of.
I tend to distinguish between liberties that I consider valuable in themselves, e.g. the right to say almost anything you like with a reasonable shot at finding an audience, the right to a fair trial, the right to a decent education, etc., and those that are administratively useful, such as most property rights, the right to leave your money to your kids when you die, the right to read Joyce to your five-year-olds, etc. I don't really have a problem with curbing the second kind of liberty if it serves any purpose and can be done predictably and systematically. (I'm a big fan of the rule of law: retroactive punishment, arbitrary seizure, etc. seem deeply wrong in themselves.) I approve of stuff like McCain-Feingold. Similarly, I don't have a problem with laws mandating that private establishments can't expel people for certain kinds of free speech, even if that seems somewhat anti-property rights.
I disagree with the linear-programming approach towards social policy, the notion that policies are best thought of as constrained optimization problems. The way I see it it's only necessary for things to work well enough, or even not terribly, while satisfying as many constraints and desiderata as one wants to impose. Arguments that some policy change would make some system less efficient tend not to move me; the relevant question is whether they would make the system intolerably less efficient. I have a similar sort of attitude toward meritocratic objections to affirmative action (though for unrelated reasons I'm ambivalent about AA itself). If the govt forces companies to employ grossly unqualified people, or makes it impossible for e.g. whites/Asians to find reasonable employment or colleges, then that's obviously a bad thing; if not, I don't much care in principle if "The Best" people don't get the best jobs. The exception to this is some areas in which there's social utility to having a rat race because it makes people work extremely long hours, which leads to socially beneficial outcomes (e.g. research/some engineering jobs); in such cases, meritocracy provides the only sensible form of organization.
In general, I don't find meritocracy (or its flip side, equality of opportunity) a useful concept. Opportunities are never going to be equal -- even if the state ran education, some kids would get the best nannies -- and in any case it's not obvious that people with better genes deserve better outcomes. (The only argument for meritocracy I believe in has to do with encouraging hard work.) Some talent will inevitably be wasted; what matters from the point of view of progress is that meaningful opportunities should exist for people with exceptional abilities, and this condition is weaker and more enforceable than equality of opportunity.
I don't think, however, that the current American educational and penal systems -- by and large -- offer meaningful opportunities even to talented poor kids in inner cities or Appalachia (never mind the third world etc.); the existence of an underclass of this kind seems to me a natural consequence of massive inequality, and also of the fact that there is, as of now, a de facto safety net for middle-class whites. If middle-class people were likelier to be locked up for trivial offences and suffered the same sorts of consequences as the urban poor habitually suffer -- if enough suburban stoners ended up with AIDS -- we might have a humane prison system. Similarly with busing and inner-city schools. The obstacle here is that it's easier for the middle class to move out, insulate itself, and use its advantage in political clout to prevent busing; and the very poor end up trapped in ghettoes. I don't see how it's possible to address this sort of thing structurally without ensuring a more even distribution of wealth -- though that is unlikely to be a sufficient condition.
One of the aspects of the communitarian critique that I find particularly interesting is the notion of the decline in the dignity of work -- in pre-industrial societies, a higher proportion of jobs required skill or strength; the fashioning of worthwhile objects gave a meaning to one's life, outside of consumption, that it is substantially harder to get out of a job at McDonald's. (As Gregory Clark points out, it seems likely that the extent of structural unemployment -- the fraction of the populace that hasn't got the skills or the ability to do any kind of job that there is the demand for -- will rise to a reasonable fraction of the populace.) This is a natural result of globalization -- there is a market for only the best books, art, and (to some extent) science; both a small community and a large one naturally sustain roughly the same number of writers, and therefore a world splintered into disconnected islands would allow for a much greater fraction of the populace to take some pleasure in their skill. What the reader gains from having access to the best stuff being done is, however, enormous [though what does that mean? I don't think it makes people objectively happier], and in the end I do believe in progress.
I started writing this down because I figured it would help me organize my thoughts; apparently it hasn't. I'll skip the bit about aesthetics for now.