The maritime industry is trying to utilize new technology for enhancing its competitiveness to overcome today’s severe economic situation, and some interact effects, or potentially emergent effects, will emerge during the introduction of these technologies. In this study, various simulations that relate to marine logistics and shipping were performed. By contrast, a detailed method that can reproduce emergent effects is required to some extent. This study utilized a Monte Carlo simulation for uncertainties, such as market and failure uncertainties. To evaluate and explore the emergent effect correctly and accurately when multiple technologies are introduced, an evaluation methodology was developed, which can evaluate the interact effect from the perspective of profit improvement and CO2 reduction during the transportation period. As a case study, decision making for introducing 28 technology combinations to the maritime industry was conducted, and the utility of the proposed methodology was assessed.