1. A method for providing recommendations related to playable content, comprising: receiving from a user of a user account authorization of at least one processing device of a plurality of processing devices associated with the user account; authorizing by an administrator of a wide area network server at least one mobile processing device of a plurality of mobile processing devices associated with the user account, the at least one mobile device being in communication with the at least on processing device; receiving a selection of one or more memories for each of the at least one processing device and the at least one mobile processing device to scan for playable content; using a scanning application on a scheduled basis to scan the selected on or more memories to locate all of the playable content that is stored within the selected on or more memories; uploading to a wide area network server data associated with all of the playable content located on the selected one or more memories scanned by the scanning application; using the uploaded data in a recommendation engine associated with the wide area network server to generate a playable content recommendation list, the playable content recommendation list referencing recommended playable content and including limited use licenses associated with the recommended playable content to allow sampling of the recommended playable content and based at least in part on user feedback concerning previously provided recommendations; providing from the wide area network sever to the at least on processing device the generated playable content recommendation list on a scheduled basis; determining an amount of available memory in the at least on mobile processing device; automatically selecting at least a subset of the generated playable content recommendation list to sync from the at least on processing device to the at least on mobile device such that the selected at least a subset of the generated playable content recommendation list does not exceed the available memory; wherein the data associated with the playable content located on the one or more memories scanned by the scanning application comprises times at which playable content was stored on the one or more memories.