Implementing multimedia in education has proven to be quite beneficial to the educational processes by enhancing the students’ cognitive abilities, accelerating of memorization and learning, and easing the understanding of abstract entities. But, for an educational system, whether it is a single institution, regional system, or even a state level system, the information that multimedia technologies provide enhancements to the educational processes is not sufficient to achieve the acclaimed advancements. To improve learning by implementing multimedia, decisions about actions and investments must be based on a specific analysis of the current condition of the educational system. In this manner, this research presents an evaluation methodology that supports the purposes of strategic planning and investments in education, in the context of advancements implementing multimedia. The methodology takes into account three key aspects: i) multimedia equipment and IT resources, ii) teacher competencies and their interest in adding multimedia to their lectures, and iii) promotional events about using multimedia in education. As a case study, the secondary school system in the city of Veles, R. Macedonia was evaluated, where the results showed the system’s strong and weak aspects, giving a profound direction in which the future enhancement efforts should be conducted.