A two-level cost management system for the transport complex is considered. On the upper level of this system is the Center, and on the lower level is the visionary executor. A theorem has been proven about the Center's optimal classification of the executor's costs into two classes using a norm configured using the Center's digital self-studying procedure. When the conditions of the theorem are met, the executor’s costs are minimized, and the best estimate of the optimal parameter that minimizes the risk of an inexperienced Center is determined. Also, the theorem has been proven about the Center's optimal classification of the executor's costs into four classes using a standard and two norms, customized using the Center's digital self-studying procedures. At the same time, the interests of the executor are consistent with the interests of the Center due to the motivation of the executor to minimize costs.