Overloaded freight vehicles significantly contribute to road damage and increased maintenance costs, posing critical challenges for road management. This paper proposes an optimal decision-making methodology that incorporates the strategic behavior of road users into Weigh-In-Motion (WIM) enforcement strategies. The objective is to effectively derive optimal WIM installation locations while minimizing pavement maintenance costs and traffic congestion. The proposed framework consists of a bi-level optimization model. In the upper-level problem, decision-makers determine the optimal WIM installation locations within budget constraints. In the lower-level problem, drivers select routes to minimize their individual travel costs. The model integrates road management and travel costs to derive a balanced WIM installation strategy. Numerical experiments demonstrated that the proposed model identified WIM installation locations that effectively balanced the pavement management and travel costs. The results indicated that the proposed enforcement strategy can reduce pavement management costs while minimizing traffic congestion, thereby enhancing the overall efficiency of the transportation network. This paper provides a strategic foundation for reducing road damage and long-term maintenance costs by encouraging overloaded vehicles to comply with the legal weight limits. The proposed methodology serves as a practical guideline for WIM installation decision-making and policy development, contributing to the effective management of road networks.