Land degradation caused by soil erosion is a major challenge in Mediterranean sloped agroecosystems, where extreme weather events and conventional land management practices accelerate soil loss and threaten long-term sustainability. This study evaluates and compares three complementary approaches to estimate soil erosion in an olive orchard in Messenia, Greece. Field-based runoff plots provided direct measurements of sediment yield, drone-based LiDAR surveys enabled soil surface change detection through the Difference of Digital Elevation Models (DoD) method, and the Revised Universal Soil Loss Equation (RUSLE) was applied to model erosion risk using site-specific parameters. Results indicate that field measurements and RUSLE estimates are broadly consistent, particularly when the model is calibrated with empirical data, offering reliable insights into soil loss dynamics. In contrast, the LiDAR–DoD approach was used to characterize soil surface displacement rather than to directly quantify soil erosion. Due to methodological and technical limitations, LiDAR–DoD results are presented primarily as a framework for future research rather than as a definitive erosion assessment tool. Overall, the integration of field monitoring, remote sensing, and modeling highlights the strengths and limitations of each method and demonstrates the value of multi-method approaches for improving erosion assessment and supporting sustainable land management in vulnerable Mediterranean landscapes.