Improving the wellbeing of Indigenous Australians remains a key challenge for regional development on Australia’s Cape York Peninsula. Indigenous Australians living in remote and rural communities such as the Cape have long been acknowledged as a marginalised group, experiencing a range of issues including joblessness, welfare dependency, ill health, poor social participation and socio-economic exclusion. Consequently, Indigenous Australians remain a target of government, industry and community initiatives designed to stimulate economic re-integration and encourage social participation. Typically, these programs focus on increasing education levels, re-skilling, encouraging entry into the labour force and stimulating business and community partnerships. However, despite a history of government spending on program implementation in remote and regional Indigenous communities, there is currently no available method by which to assess the progress and success of these engagement initiatives. This paper is based upon a case study review of key performance indicators used to measure wellbeing of other selected disadvantaged groups such as low-income or marginalised peoples (e.g., migrants, females and the poorly skilled). The overarching aim of this project is to inform decision makers of the way(s) in which economic (re)-integration programs can be assessed and improved to better target future governmental spending and optimise program implementation in programs for economic and social (re)-integration of Indigenous persons on the Cape York Peninsula. Key learning experiences from this project include an identification of the impediments and facilitators in performing such evaluations; and ways in which to address existing gaps in the key socioeconomic datasets already available for the Indigenous communities of the Cape. Many of the challenges faced by the Cape York Peninsula in attempting to (re)-integrate into the Australians economy are shared by other disadvantaged community sectors. Hence, this study is relevant to such community sectors and could assist policy making for a range of Indigenous and other disadvantaged communities.