In this work, we propose a data-driven skill-informed framework to design optimal haptic nudge feedback for high-dimensional novel motor learning tasks. We first model the stochastic dynamics of human motor learning using an Input-Output Hidden Markov Model (IOHMM), which explicitly decouples latent skill evolution from observable kinematic emissions. Leveraging this predictive model, we formulate the haptic nudge feedback design problem as a Partially Observable Markov Decision Process (POMDP). This allows us to derive an optimal nudging policy that minimizes long-term performance cost, implicitly guiding the learner toward robust regions of the skill space. We validated our approach through a human-subject study ($N=30$) using a high-dimensional hand-exoskeleton task. Results demonstrate that participants trained with the POMDP-derived policy exhibited significantly accelerated task performance compared to groups receiving heuristic-based feedback or no feedback. Furthermore, synergy analysis revealed that the POMDP group discovered efficient low-dimensional motor representations more rapidly.