This article examines the contradictory proposed connections between compact urban form and small housing and human well-being. Whereas planners have argued the merits of smart growth and more compact urban form, compared to the traditional North American sprawling suburb, since at least the 1990s, other researchers and the global urban development community have more recently added their own evidence and argument in order to understand how not just the land use dimensions but also the transportation infrastructure design, greenhouse gas emissions profile, and social and personality characteristics may be more favourable in a compact, infill urban context than in a suburban or sprawling context. At the same time, the connection between compact urban living and well-being is not clear to many, as suburban style development expands at a faster rate than compact urban development in much of the world. Moreover, compact urban form is increasingly criticized for exerting downward pressure on liveability and well-being by exacerbating unaffordability. Taking a case based focus on the Metro Vancouver region in British Columbia, well-known for its liveability advantage and compact urban form, we present the results of survey research on resident attitudes toward and perceptions of moderate density housing being added within existing neighbourhoods. We find evidence of a tipping point, at which attitudes about new compact housing may hinge on the possibility for existing residents to have a voice in new developments and on the rate of change as much as on design or structural characteristics of the development. Perceptions of the contribution of more compact urban form and housing options to well-being should be considered central to efforts to advance such housing forms and types in cities, if these efforts are to pass the test of public opinion.