This article addresses issues related to the quality of design and subsequent management of multi-family residential buildings in the context of their energy supply. The framework of the analysis carried out here are pro-environmental legal regulations currently in force in Poland. This article describes the impact of these regulations on the design process and the role of the designer. The requirements have been defined and the constraints have been identified. A number of factors directly related to the nature and parameters of the designed buildings and their location have been taken into consideration. On the basis of this study, the impact of legal regulations both on the method of energy supply in the buildings and on their later use and management have been presented. Positive and negative aspects of the analyzed regulations have been indicated and directions for their evaluation and optimization have been proposed. The research was carried out using real buildings, both completed and in the design phase. This article is based on the authors’ extensive experience in designing multi-family residential buildings in Poland.