When searching for the right life insurance product, one can either confide in her/his insurance broker or fill out lengthy questionnaires at Internet Portal sites before gathering a large amount of knowledge for interpreting the results. While the first alternative is risky, the second is cumbersome. In this paper, we present an approach that overcomes these drawbacks. It makes use of Structural Case-Based-Reasoning (SCBR) extended by the concept of generalized cases. Here, each insurance product is represented as a generalized case and therefore similarity assessment and indexing of case bases consisting of generalized cases is one of the topics of this paper.