Great work Jason!
I was amazed of the beauty of Wordie but then I loved Darth Vader (Figure 3-11. Do not underestimate the power of the randomized greedy algorithm). The words reuse should definitely need to be allowed, but the result will be very beautiful when applied to smoothly changing contour (shape).
Is there a problem if I try to reimplement your code in C++ (especially openframeowks)?