Over the past few decades, there has been considerable transformation of the organizational arrangements for public service provision and advocacy across most Western democracies, particularly in Australia. Waves of ideologically driven reforms have reshaped organizations, ways of organizing, and systems, especially those in the third sector. Each wave has produced specific synergies and contradictions that contribute to the need for further reshaping. As artifacts, local organizations, ways of organizing, and systems hold historic meaning that can guide practitioners as they seek to understand past change, traverse existing landscapes, question the utility and soundness of current meaning, and seek to create new landscapes that respond to different value sets. The studies presented here were undertaken by the authors over two decades in partnership with local practitioners to respond to the challenges faced.