Okay so the following keyboard shortcuts are helpful but don’t fully resolve the issue:
uu => Expands all animated tracks so that keyframes are visible.
k => Advances the current time indicator to the position of the last visible keyframe.
So the procedure now looks like:
Paint a stroke.
Press uu.
Press k.
Repeat
Again, my goal would be to simply draw the image in one go and then have after effects rebuild it after the fact. Not unlike painting it in photoshop with a screen capture program running.
I guess another option would be some sort of plugin that always advances the time slider to the position of the last keyframe anywhere in the layer would be helpful; but I don’t know if AE supports that sort of plugin.
Thanks,
Donovan