Gentrification and urban regeneration processes in Vancouver, Canada, provide a compelling case study that highlights neo-liberal North American development trends as supported by the broader gentrification literature. We argue that Vancouver both exemplifies and challenges prominent themes and observations of urban renewal, and adds to our understanding of the changing cityscape through its unique demographic and cultural trajectory. We argue that post-industrial Vancouver is representative of a ‘new economy’ of work as an emerging ‘cultural class’ of young professionals whose lifestyle, income, consumption practices and ideology have helped to prop up policy and planning initiatives aimed at creating more livable, high density, communities. Vancouver’s achievements in urban sustainability and mega-project completion, including the legacy of Vancouver’s 2010 Winter Olympics, also resulted in increased socioeconomic disparities by design as planning agendas and local political processes prioritized the needs and interests of affluent populations over the disadvantaged. The top-down approach to urban regeneration is certainly not unique to Vancouver, and many of the outcomes could have been predicted based on the broader urban regeneration literature. At the same time, the redefinition of livability as a measurement for successful gentrification initiatives is an important frame of reference for future research, and we advocate its inclusion in future research on the changing dynamics of North American urban centers.