Ray tracing has become a standard for accurate radio propagation modeling, but suffers from exponential computational complexity, as the number of candidate paths scales with the number of objects raised to the interaction order. This bottleneck limits its use in large-scale or real-time applications, forcing traditional tools to rely on heuristics that reduce path candidates at the cost of potentially reduced accuracy. To overcome this limitation, we propose a machine-learning-assisted framework that replaces exhaustive path searching with intelligent sampling via Generative Flow Networks. Applying these generative models to this domain presents challenges, particularly sparse rewards due to the rarity of valid paths, which can lead to convergence failures and trivial solutions when evaluating high-order interactions in complex environments. To ensure robust learning and efficient exploration, our framework incorporates three key components. First, an \emph{experience replay buffer} captures and retains rare valid paths. Second, a uniform exploratory policy improves generalization and prevents overfitting to simple geometries. Third, a physics-based action masking strategy filters out physically impossible paths before the model considers them. Validated on idealized street-canyon scenarios, our model achieves substantial speedups over exhaustive search -- up to $10\times$ faster on GPU and $100\times$ faster on CPU -- while maintaining high coverage accuracy and successfully uncovering complex propagation paths. However, out-of-distribution evaluations on real-world Manhattan street geometries reveal that generalizing to substantially different urban morphologies requires further advancement in model capacity or alternative training strategies. Source code, tests, and a tutorial are available at https://github.com/jeertmans/sampling-paths.