Maintenance decisions at the end of building components’ service life are frequently driven by subjective motivations. Subjective motivations can arise from various sources, including the building owner’s personal preferences, sentimental attachments, aesthetic considerations and individual/collective preferences or sense of taste. It is important to acknowledge that subjective motivations for maintenance decisions, beyond technical requirements, hold value as they reflect the human element and emotional connections associated with buildings. Balancing these subjective motivations with technical considerations (e.g., original design intent) and financial constraints is essential for making well-informed decisions that address both practical needs and emotional connections. In this study, a digital model is proposed to assess the degradation state of buildings’ coatings, based on in situ inspections (using robotized platforms and a high-resolution camera), while engaging the building's occupants, tenants, or users to understand their perceptions, experiences, and concerns regarding the building’s condition. A stains’ detection algorithm, using multispectral analysis, is developed to identify the area affected by stains (a visible sign of degradation), which affect the facade’s aesthetic appearance but also contribute to the worsening of other anomalies and consequent degradation and loss of properties of the coating. This study enables the identification of patterns, correlations, and discrepancies between objective degradation indicators and subjective user feedback. The dwellers’ feelings are modelled based on onsite interviews to collect qualitative data on their observations and satisfaction levels. This study supports decision making regarding maintenance actions by combining objective indicators of building degradation and the subjective user perceptions to prioritize areas of focus, determine appropriate maintenance strategies, and allocate resources effectively.