What do you mean by "So far all I seem to be able to do is get the animations all happening at the same time: all my list items start and finish their animation at the same time"?
I've got my banner set up at the top and underneath I have 1 - 5 of the points I want to express. The banner is static: it doesn't move. The points 1-5 appear using an animation. What I want to do is put each point on a separate animation, starting and finishing at different times. I can't seem to make use of keypoints for this.
You can animate the banner if it is a separate title and graphic on a separate video track.
Just know going in that this is a pretty major animation job you're attempting! It's not impossible by any means, but there's no easy way to do it. That's why this time of complicated animation is usually done in a high-level program like After Effects (which was most likely what they used to create Letterman's animations).