A hybrid computer-based system and method for scheduling a plan of training programs, such as flight training programs, is disclosed. A heuristic scheduler receives a plan request comprising training programs to schedule, along with a plan vector, scheduling rules, and available resources. The scheduler computes a locally optimized scheduling plan of the training schedules in the request. An evaluator evaluates one or more costs of the scheduling plan. A solver employs stochastic methodology of reordering the plan vector, in order to improve the costs. The scheduler, evaluator, and solver are employed iteratively until a globally optimized scheduling plan is determined. In some embodiments, scheduling rules are arranged in a sequence of constraint-relaxed tiers, allowing for flexibility in heuristic scheduling in light of multiple layers of constraints: validity, i.e., inviolable (hard) constraints that training schedules must meet.