arXiv:2604.14206v1 Announce Type: new Abstract: This paper proposes a machine learning assisted portfolio optimization framework designed for low data environments and regime uncertainty. We construct a teacher student learning pipeline in which a Conditional Value at Risk (CVaR) optimizer generates supervisory labels, and neural models (Bayesian and deterministic) are trained using both real and synthetically augmented data. The synthetic data is generated using a factor based model with t copula residuals, enabling training beyond the limited real sample of 104 labeled observations. We evaluate four student models under a structured experimental framework comprising (i) controlled synthetic experiments (3 x 5 seed grid), (ii) in-distribution real market evaluation (C2A) and (iii) cross-universe generalization (D2A). In real-market settings, models are deployed using a rolling evaluation protocol where a frozen pretrained model is periodically fine tuned on recent observations and res...