@Evil so I'm thinking take the first image and "subtract" it from the second image. This will leave me with all additional lines needed to create the 2nd image. Now I need to categorize the remaining lines.
I'd start by selecting all isolated lines and saying that these can be added at any point in the animation. So the remaining lines must all be connected. For these connected lines, one idea I have is to calculate its length, divide it into like 8 parts or something, and then animate the pencil going over the line segments one at a time. What do you think?