Alright, so I tweaked the CV a bit, putting "Honors & Awards" on page 1, not page 3. I cut down my references list from 11 to 5. I cut out extraneous details (like the city of publication for journals I've published in). Finally, I added a separate heading for Conference Panels that I've organized and/or chaired.
I also completely rewrote a new cover letter, expanding to two full pages. I detailed more about what my dissertation accomplished. I wrote two whole paragraphs on my current and planned research agenda. I included three paragraphs on my teaching, lectures, conference presentations, and other public activities, talking about courses I've taught, new courses I propose, and my general approach and philosophy to the subject matter.
My dissertation chair (yes, I got him to email me!) suggests that I work a bit more on the opening paragraph (since it may be the only one they read) to be "more of a summary and less of an introduction." As he puts it:
In general, I find it better when people speak of their enthusiasms rather than their accomplishments, and use a cover letter to do the kinds of things you can't do in a CV; that is, convey the flavor of the applicant and their thought.
This one goes out to an Ivy League school tomorrow. Wish me well.