We introduce a framework for analyzing topological tipping in time-evolutionary point clouds by extending the recently proposed Topological Optimal Transport (TpOT) distance. While TpOT unifies geometric, homological, and higher-order relations into one metric, its global scalar distance can obscure transient, localized structural reorganizations during dynamic phase transitions. To overcome this limitation, we present a hierarchical dynamic evaluation framework driven by a novel topological and hypergraph reconstruction strategy. Instead of directly interpolating abstract network parameters, our method interpolates the underlying spatial geometry and rigorously recomputes the valid topological structures, ensuring physical fidelity. Along this geodesic, we introduce a set of multi-scale indicators: macroscopic metrics (Topological Distortion and Persistence Entropy) to capture global shifts, and a novel mesoscopic dual-perspective Hypergraph Entropy (node-perspective and edge-perspective) to detect highly sensitive, asynchronous local rewirings. We further propagate the cycle-level entropy change onto individual vertices to form a point-level topological field. Extensive evaluations on physical dynamical systems (Rayleigh-Van der Pol limit cycles, Double-Well cluster fusion), high-dimensional biological aggregation (D'Orsogna model), and longitudinal stroke fMRI data demonstrate the utility of combining transport-based alignment with multi-scale entropy diagnostics for dynamic topological analysis.