After getting some excellent feedback via both Twitter and ENWorld.org, here is the revised Skill Challenge Tracker:
It is now a full 8.5" x 11" and more printer friendly (less areas of solid black). Additionally, there is now a place to visually keep track of successes and failures as well as extra room for notes, etc.
Assuming I don't receive any further groundbreaking feedback, I will begin converting this into a pdf with editable fields. I hope to have this completed by the end of the week, but no promises.