This article brings together ethnographies of two privileged educational settings in the United States--a private school in California's Central Valley following the progressivist Sudbury model, and an affluent New England boarding school's summer enrichment program. Each of these institutions serves as an alternative to and/or extension of publicly accessible education institutions during a neoliberal era of marketization and growing educational inequality. By comparing findings from ethnographic studies of each institution, we find that both celebrate open access and socially responsible pedagogical values in ways that obscure mechanisms of exclusion and an entrenched individualist ideology. We discuss two particular contradictions that manifest in both settings: first, a discourse of openness and inclusivity that belies the ways in which access is mediated by constructions of who best "fits" the special learning community; and second, an outspoken allegiance to socially engaged values of diversity and democracy that belies the ways in which these values are commodified and appropriated for students' individual advantage(s). In comparing such sites, we argue for the importance of tracing the mechanisms of advantage in under-researched "niches" of the dynamically shifting and unequally accessed neoliberal marketplace for educational opportunity.