Prompt 1:
This drawing tool, in a physical form, feels like what a modular stamping tool would be like. The different shapes you can stamp are limited and can be selected from in the dropdown menu, like attachments you would swap at the tip of the tool for each shape. This tool is already not too practical for broad use in typical drawing since its for stamping one shape at a time, and this is further reinforced by the random color button, which would be a button on the pen, too, to switch the color of the stamped shape. This is obviously an artistic quirk of the tool making it less optimized for recognizable drawings, but rather for something more random. It would take considerably less time and effort to use the tool randomly by stamping different shapes of varying color, orientation, and scale all over a canvas for a visually pleasing final product. The rotation and scale sliders in the drawing tool may be implemented as twistable or slideable analog pieces that correspondingly rotate and scale the shape of the stamping tool. As for how the empty/filled shape mechanic would be implemented into the physical tool seems less intuitive. I think the most natural way this mechanic translates into the physical tool would be application of pressure with the tool on the canvas. As shapes in the lower half of the digital canvas are empty, pressing the physical tool against the physical canvas with lower amounts of pressure would result in the outline of a shape rather than it be filled, and vice versa for the higher shapes.