Hi AM:
If you have the Designer Edition upgrade ($49.99) to the Silhouette Studio software you can create layers that you use to separate objects to make them easier to manipulate. You would move the scanned image into one layer and then lock that layer so you can't move the image. Then you draw your masks in another layer (or layers). You can break down complex drawings that involve many small masks close together (think the shark mouth on a Flying Tiger P-40) into layers (mouth outline, tongue, teeth, etc.) so you can draw all the elements over one scanned image but print each layer as a separate mask. There a number of other useful tools in the Designer Edition that I think makes the upgrade worth the money. See https://www.silhouetteamerica.com/software/silhouette-studio-features-comparison-chart for a comparison of each upgrade. Unfortunately you have to purchase each upgrade in sequence, you can't skip an upgrade to save money.
Good luck with your project.
Wrongway_Joe
