This chapter presents the challenges, opportunities, and insights derived from monitoring, assessing, and learning within urban transformation processes in the Desire project, aligned with the values of the New European Bauhaus (NEB). Focusing on local site experimentations, the chapter explores complex socio-ecological systems, highlighting three assessment dimensions: embracing challenges, empowering choices, and enabling change. The Desire monitoring, assessment, and learning framework combines the logic model with outcome mapping, fostering adaptive, reflexive learning through three distinct modes—learning-by-doing, learning-by-interacting, and learning-through-reflection. The results reveal the importance of inclusive, multi-stakeholder processes to address sustainability, inclusivity, and aesthetics, with special attention to diverse local conditions, participatory decision-making, community engagement, and organizational change. Despite challenges with tracking progress and aligning stakeholder expectations, the Desire site experimentations contribute valuable knowledge on collaboratively developing sustainable urban environments. This chapter underscores the critical need for assessment frameworks that can guide inclusive, adaptable, and responsive processes to complex social and ecological needs, providing a foundation for future urban transformation efforts.