The complexity of today's enterprise application landscapes makes the selection of new applications which still fit into the existing landscape a complex and daunting task. In this paper, we present an approach to support this task by a two-phase landscape-dependent evaluation process. In the initial phase single characteristics of the landscape's different applications and the application to be introduced are assessed. In the second phase these characteristics are combined into an overall value which can be regarded as an indication of how adequate the new application will be in the context of the existing landscape. We rely on vague evaluation models for the calculation of this indication and present fuzzy logic as one example for such a model. Finally, we substantiate our approach by a practical example.