Hey Kids! Squiggly Draw!
I did it in Sketchup (using WoodGears Gear Generator).
There are two series of holes. One for small narrow markers and stuff and another for big fat ball points. Both the acrylic and hardboard are 1/8″ thick material.
As you can see in the pictures it is a blast.
If anybody would like the source files, feel free to ask and I’ll post here. squiggly