Seniors will make up an unprecedented 25% of Canadians by the year 2030. This demographic shift will challenge our society to address the basic human right of a dignified and healthy aging. One troubling aspect of aging is the degree to which seniors experience isolation and loneliness. Cohousing can offer older adults a place to age in place, within a 'community-of-care'. However, the challenges of creating senior cohousing are numerous - the failure rates staggering. What factors contribute to this challenge? What could the way forward look like? This thesis searches for answers in the perspectives of professionals representing sectors of the development process. Interviews were conducted with experts in: non-profit housing, housing policy, development consulting, and private real-estate. Focusing on urban senior cohousing in Ottawa, Convivium Cohousing is used as a case study to ground the theory. It is expected findings will transfer to other parts of Canada.