In recent years, deterioration of expressways is the serious problem, and it is necessary to plan the medium and long term management policy. In this study, the authors examine the medium and long term management policy, using the accumulated enormous inspection data of road surface conditions. The future condition of road pavement is significantly different by the management system such as the budget, personal distribution or repair method, etc. The authors quantitatively evaluate the relation between the future condition of road pavement and the management system, of which the authors specially take up preventive repair by penetration repair agent. Then, the risk evaluation and the life cycle cost (hereinafter referred to as LCC) analysis can be conducted in deferent repair strategies by stochastic simulation. By using stochastic simulation as the method of these two evaluations, the comprehensive analysis can be conducted, considering the possible change of management surroundings in the medium and long term and various examinations for optimization.