If I were able to do it, I would simply add a new management page under Design called Page Images or something like that. Allow for image file uploads, including resizing to the site's current standard sizes. Once they're up there, I can teach my clients how to use the URL field in the Image tool of CKedit.
That should be a quick addition, and I'd be willing to fund it. Even more so if the images were accessible directly when editing a product, category or content page.