Oohhhh, I remember that waitlist well!!!! I was waitlisted at Stanford Med 3 years ago. Basically I was one of those ppl who didn't even get looked at by the big schools like Harvard, JHU, Penn, etc, b/c of my weak MCAT score. I got interviewed by 3 schools (one of whom was Stanford), got into the 2 others (one was top 20 at the time, now it's top 15--which is where I ended up going), the other was like a top-30 school. Stanford would have been my ultimate number 1 choice had I gotten in. I send about 3 letters with updates and telling them of my interest. I called a couple of times (maybe I should have called more). Basically even though Stanford started later than the school I matriculated at, I still had hope that I'd get the phone call that I was off the wait list, and I actually called them one last time when I'd already started my med school. Maybe it's against the rules, but I didn't know that. But anyway, the administrator I talked to at Stanford must have known I'd already started at this other place, and she sounded pretty annoyed and mean to me. She actually told me somebody got off the waitlist, but that it wasn't me, and she was like "go ahead and go to the other places you got into."
Anyway, I have not a single regret. This may be a rationalization, but in fact I think it was a miracle that I didn't get into Stanford, b/c I may have ended up on one of those planes that were hijacked on Sept 11th, God forbid. I love my med school and wouldn't trade it for any other!!