Measuring and communicating the holistic value of community arts and wellbeing initiatives is often difficult, time consuming, and depending on the method, can miss important intentions and outcomes. But without some form of criteria and evaluation, communities and decision-makers may not know what to prioritise and invest in. This chapter reflects on my involvement in developing approaches to assess and evaluate the investments (or intentions) and the returns (or outcomes) of the transformative work carried out by the non-governmental place-making and artist-enabling organisation Life in Vacant Spaces. This experiment in shifting evaluation practices away from individualising and reductionist assessments provided holistic and engaging communications of value for communities, funders, and social enterprises.