There appears to be a glitch with the html editor manager that causes it to remove the settings for the max file size and max document size. I found a link here: http://www.dotnetnuke.com/Resources...age/1.aspx
Which has the solution in it. The solution is to edit the configuration file for the rad editor manually and bypass the html editor manager. This solved my problem as well as a few others.
DesktopModules\Admin\RadEditorProvider\ConfigFile and open configfile.xml. You need to add values (mine were blank) for MaxImageSize and MaxDocumentSize and that should fix it. These should be around lines 28 and 31
83886080 bytes = 80 MB