Insurance coverage on valuable personal property (“VPP”) can be marketed and/or serviced through an expert system that interacts with a user through a web site and web browser. VPP coverage tends to have many facets and complexities, and a system can be used to explain the various complexities and to guide said user through the process of selecting coverage, obtaining a quote, and purchasing said policy. The system can provide various forms of user education, such as graphical and/or text screens that explain features of coverage, can also provide said user with a linear process flow for those tasks that can be accomplished simply, and can involve a human representative for more complicated tasks.