The healthcare environment presents a large volume of personal and sensitive patient data that needs to be available and secure. Information and communication technology brings a new reality to healthcare, promoting improvements, agility and integration. Regarding high-level and complex decision-making scenarios, the Brazilian Navy (BN), concerning its healthcare field, is seeking to provide better management of its respective processes in its hospital facilities, allowing accurate control of preventive and curative medicine to members who work or have served there in past years. The study addresses the understanding, structure and clarifying variables related to the feasibility of technological updating and installing of a Hospital Information System (HIS) for BN. In this scenario, through interviews and analysis of military organization business processes, criteria and alternatives were established based on multi-criteria methodology as a decision aid. As methodological support for research and data processing, THOR 2 and PROMETHEE-SAPEVO-M1 methods were approached, both based on the scenarios of outranking alternatives based on the preferences established by the stakeholders in the problem. As a result of the methodological implementation, we compare the two implemented methods in this context, exposing the Commercial Software Purchase and Adoption of Free Software, integrated into Customization by the Marine Studies Foundation, as favorable actions to be adopted concerning HIS feasibility. This finding generates a comprehensive discussion regarding the BN perspective and changes in internal development in the military environment, prospecting alignment to the culture of private organizations in Information Technology for healthcare management. In the end, we present some conclusions concerning the study, exploring the main points of the decision-making analysis and for future research.