Systems and methods of replacing digital assets within a multimedia document are provided. The systems and methods include a user workstation that can receive a selection from a user for an original asset in the document to be replaced. Alternative assets can be retrieved that have a level of appropriateness with the selected original asset. Constraints on use of the alternative assets can be determined and a fitness value of each of the alternative assets can be calculated based on the appropriateness and the constraints on use. The alternative assets with the highest fitness values can be presented to the user for the user to select to replace the original asset.