Monitoring avocado (Persea americana Mill., cv. Semil-34) in tropical mountain landscapes of Cambita, San Cristóbal, Dominican Republic is inherently complex due to the pronounced topographical and climatic heterogeneity that modulates the crop’s ecophysiological responses, specifically vegetative vigor, carbon allocation, and the synchronization of reproductive flushes. This study integrates 5-year (2020–2025) Sentinel-2 time series, ERA5-Land climatic variables (air temperature, total precipitation, and radiation), and geomorphometric covariates to explain variability in yield and fruit quality. Multispectral indices, including the Normalized Difference Vegetation Index (NDVI), Enhanced Vegetation Index (EVI), Normalized Difference Red Edge (NDRE), and Normalized Difference Moisture Index (NDMI), were analyzed using Partial Least Squares Regression (PLSR) to characterize phenological dynamics and rank dominant predictors. The results revealed coherent spectral phenological trajectories; however, a significant inverse relationship was detected between canopy vigor and yield during reproductive phases. High vegetation index values were significantly and negatively associated with lower production (r = −0.58, p < 0.0021), reflecting a potential source–sink imbalance. Topography functioned as a structural filter, regulating root drainage and productive stability across the landscape. While yield variability was partially explainable (R² = 0.38), internal fruit quality, measured as dry matter content, exhibited comparatively high environmental stability. A central contribution of this research lies in identifying the “vigor paradox” in cv. Semil-34 and the suggestion that topography may exert a stronger influence than direct spectral signals under tropical hillside conditions. These findings provide an exploratory framework for anticipating yield and fruit quality through satellite remote sensing or UAVs, supporting site-specific management decisions in mountain agricultural systems.