Farm level changes tend to be connected with alterations in markets (and food chains) on the one side, and with the prosperity of the rural areas in which they are embedded on the other. They are inherently linked to the underlying logics of agro-economic and food systems. Technical 'solutions' often only alleviate the symptoms and ignore wider ramifications. In this paper, we argue that decisions in both, the private and public sector need to pay attention to the systemic nature, and dynamics, of processes, interactions and impacts. The main focus is on rural prosperity, the different ways of understanding the concept and the related parameters and strategies. The discussion incorporates key elements of social learning as well as a range of rural development models. In the analysis, we will examine different farming systems through the "Working with People" model. The basis for the analysis are major case studies from six countries with data from interviews with key actors and stakeholders, focus groups and data on indicators of rural prosperity and wellbeing.