Lindsey, you accurately depicted the fictional life of Waldo that has led many people to wonder "Where is Waldo?". The rush of life, the various persona's, all the possibilities as to where and who Waldo might be are perfectly presented in your essay. I can't fault what you have written because it is really an interesting take on the given topic. However, I think that the prompt can be addressed in a more personal manner that still relates to "Waldo".
Have you ever considered that the prompt is asking you to find Waldo within yourself? Try to think back to the various times when you have wanted to escape from your regular life in search of adventure or more meaning. Isn't that what Waldo seems to be doing by traveling the world and allowing people to search for him? You said so yourself
What if Waldo is just trying to find himself?
My approach to this essay would be from this angle. However, I would place myself, or in this case, you, at the center of the adventure and describe a sense of self-discovery as personified by Waldo. Call yourself Waldo for this essay. Place yourself in the adventure and ask yourself, why would Waldo (you) be constantly running across the globe? What is he looking for? Can he find it? Assume that you have gone on the voyage of self-discovery and you have come to learn where Waldo is within you, end the essay on that note.
The strength of this essay should lie in the fact that you have found your personal "Waldo" and come to accept her. Why did Waldo have to go on the adventure? What did he discover along the way? Finally, where was "Waldo" finally found? These are questions or concepts that could liven up the essay and give it a fresh response coming from your end. It just may liven up the interest of a reviewer who is already jaded by the common responses that come with this prompt. Perhaps you would like to try writing this essay from a new perspective? This is an interesting topic that can be dealt with in numerous ways as an essay. Your approach was one and my suggestion is another one. Whatever way you choose to approach the prompt, I know you will write it in the manner that you feel best suits your needs.