Housing and sustainable development is interdisciplinary research that requires cross functional knowledge-sharing to address operational and policy issues—limitations in understanding housing dynamics and policy design and implementation lead to unintended negative consequences. Policy development for affordable housing requires better conceptual understanding, determination of normative objectives and operational constraints, and the effectiveness of governance structure. This paper investigates operational and governance barriers to housing affordability in the Canadian context. The article adopted a key informant interview method to analyze qualitative feedback from technical and administrative experts from the municipalities across Canada. The study helped to understand the contextual challenges in housing affordability in Canadian municipalities. The study confirms that the weaknesses in governance structure, distribution of responsibilities, and allocation of resources limit municipalities' capacity to deal with housing affordability. Pro-growth objectives will not solve housing affordability challenges. It is important to adopt human centered and contextually relevant housing policies. To overcome operational constraints, municipalities need more significant provincial and federal financial and constitutional assistance to meet capacity challenges and to guide a unified approach to meet sustainability targets.