Due to the ongoing digitization, digital libraries are used more and more by art and architectural historians. Nevertheless, the design of those platforms does not necessarily meet the expectations and user requirements of the scholars. This is especially valid for digital libraries dedicated to historic media such as photography. In this article, we aim to analyze the user community in a first step, in order to see from which fields of interest they come and how far developed their computer affinity is. In a second step, the user requirements of the scholars will be examined, specifically with regard to research questions of architectural history. Based upon those observations, in a third part a possible technical solution will be proposed that could facilitate the work with digital libraries as well as the research process. A case study on the question of the correlation between urban development and the perception of the city will give a further validation of the analytical parts, showing the deficits of yet existing digital libraries and highlighting starting points of further research support.