Has any thought been given to using a chunked upload library like plupload to eliminate the file size issues? Currently, we have to enable FTP access for professors to upload media files larger than php will allow in one chunk. Using plupload would allow larger files by splitting it into chunks, showing a progress bar and reducing memory usage on the server.
Wordpress is including this library in version 3.3. A widget exists for Drupal. It just seems like a good idea...