Andrew, what Mindy did is precisely what I outlined in my answer, but asked you to hold off doing until Jamie had an opportunity to figure out why the problem happened.
You don't have to upload the same image to each page you want to display it on. Once an image is on any page, you can go to the image's page by clicking on it anywhere it is displayed (like in the main section of your space page). On the image's page, you can attach more pages to the image and you can also designate the image to be primary on any of the pages attached to it. "Primary" means that a thumbnail (a small version) of the image is displayed in that top left space on the page.