Rumen's solution of changing the EditorDialogs worked for me. We also wanted to update the documents already in the RadEditor, so I added a tool to update the images. Here is the relevant jquery that I used:
function refreshImages(editor) {
var newID = Math.random();
var hTML = editor.get_html(true);
var $html = $(hTML);
$html.find("image").each(function (i) {
var src = $(this).attr("src");
if (src.indexOf("?") > 0) {
src = src.substring(0, src.indexOf("?") + 1) + "param=" + newID;
} else {
src += "?param=" + newID;
}
$(this).attr("src", src);
});
editor.set_html($("<p>").append($html).html());
}