The main goal of the study is to develop a complex hybrid model for evaluating projects to improve the sustainability and health of regions and cities within the European Green Deal and Industry 5.0 concepts. The complex model is a comprehensive evaluation system that considers various influencing factors, the investor’s intentions regarding the need and financing of projects, as well as expert opinion on the possibility of achieving sustainability and health of regions and cities by implementing this project with the investor. The model is based on modern theory of intellectual knowledge analysis, fuzzy set theory, and systems approach. Furthermore, we have an initial quantitative assessment and the linguistic significance of the level of the project financing decision with a reliability assessment. The knowledge from the repository of 896 project plans in the field of transport submitted for implementation and financing in the period 2021–2027 was used for the creation of the model. The results of the study were tested on the examples of evaluation of five real projects and demonstrated the applied value of the methodology for evaluating the level of decision-making feasibility of project financing in uncertainty and the importance of making correct management decisions based on expert opinions.