The repeated extraction of coal seams in the Loess Plateau mining region has greatly increased the severity of surface deformation and associated damage. Accurately characterizing the spatio-temporal evolution of subsidence and the underlying mechanisms is a critical engineering challenge for mining safety. Taking the Dafosi Coal Mine located in the loess gully region as a case study, this paper thoroughly examines the variations in surface deformation and damage characteristics caused by single and repeated seam mining. The analysis integrates surface movement monitoring data, global navigation satellite system (GNSS) dynamic observations, field surveys, unmanned aerial vehicle (UAV) photogrammetry, and numerical simulation methods. Notably, to ensure the accuracy of prediction parameters, a refined Particle Swarm Optimization (PSO) algorithm incorporating a neighborhood-based mechanism was employed specifically for the inversion of probability integral parameters. The results indicate that the subsidence factor and horizontal movement factor increase markedly following repeated mining. The maximum surface subsidence velocity also increases substantially, and this acceleration remains evident after normalizing by mining thickness and face-advance rate. The fore effective angle is smaller in repeated mining than in single-seam mining, and the duration of surface movement is substantially extended. Repeated mining fractured key strata and caused a functional transition from the classic three-zone response to a two-zone connectivity pattern, while the thick loess cover responds as a disturbed discontinuous-deformation layer, which together aggravates step-like and slope-related damage. The severity of surface damage is strongly influenced by topographic features and geotechnical properties. These findings demonstrate that the proposed integrated approach is highly effective for geological hazard assessment and provides a practical reference for engineering applications in similar complex terrains.