Systems, graphical user interfaces and methods for upgrading from one or more digital media assets to a set of digital media assets over a network are described. A potential purchaser can be notified of available upgrade opportunities that are available for purchase. The potential purchaser can elect to pursue an upgrade opportunity so as to purchase a set of digital media assets. Upon upgrading to the set of digital media assets, the digital media assets within the set of digital media assets are made available to the purchaser. According to one aspect, a graphical user interface facilitates presenting and requesting upgrade opportunities. According to another aspect, equivalency rules and/or eligibility rules can be used to control which sets of digital media assets are available for upgrade by respective potential purchasers.