In agricultural landscapes, humans impact the environment through land use change, causing natural resource depletion and potentially reducing crop and animal production. These changes, in turn, can impact the livelihood and food security of the rural population, and lead to socio-economic changes such as induced marginalization and land abandonment. In Mesoamerica, rural development policies aimed at intensifying agriculture in detriment of traditional indigenous systems. These policies are expected to have an impact on rural landscapes and its people, and understanding this intricate interaction is key for assessing household, community, and landscape trajectory. Therefore, this thesis aimed to assess these trajectories as affected by several drivers of change and to evaluate current landscape performances in terms of ecosystem services and food provision to propose landscape alternatives for improving food self-sufficiency without sacrificing other ecosystem services. This study was performed in the geo-cultural Mixtec region in south Mexico, and two municipalities were selected for in-depth analysis. The thesis is divided into four main chapters. First, I assess livelihood strategies and household typologies as affected by migration, government support, and changes in land tenancy policies. Second, I evaluate landscape change at the watershed and municipal level and link these changes to socio-economic and environmental drivers. I then highlight how communities manage their landscape according to their context-specific conditions, demonstrating that regional drivers of change might not be enough for describing land use change. Third, I evaluate changes in food self-sufficiency over time and show the nutritional advantages of milpa, an indigenous polycropping system, over the predominant monocrop of maize and bean. In the last main chapter, I assess the current landscape performance in terms of several nutritional, environmental and socio-economic indicators to propose landscape configurations that asses multiple stakeholder objectives in conjunction.