This article presents the issue of sustainably managing of the technical maintenance of multi-family residential buildings with diverse characteristics. The results of this research conducted on entities managing real estate in a real estate market in the city of Poznan (0.5 million inhabitants) are presented along with comments, with attention drawn to the commonness of the approaches used in building maintenance management. Of particular note is the reactive approach (which, in extreme cases, turns out to be unreliable and does not guarantee the absence of restrictions in the possibility of using housing resources) and the practical lack of application of the proactive-predictive approach. The main features of the approaches used in management are presented, and selected examples are used to demonstrate the advantage of proactive approaches in the economic, social, and environmental aspects. This article presents arguments for the implementation of proactive management strategies, including predictive maintenance. Due to financial and technical limitations, our model is presented in support of the technical management of buildings with predictive elements. The model is based on case-based reasoning (CBR). An important element of the model is the knowledge acquisition system, which uses mandatory technical condition inspections resulting from the applicable law and inspection protocols created as a result. The proposed model is not as expensive as using full predictive maintenance using sensor infrastructure devices, and at the same time allows advanced reasoning and solves the practical problems of maintaining housing resources.