Not sure #1 is capable of being setup easily, because it would have issues with handling new revisions of the file. You could probably set up the WebDav server option and just upload a small file initially, then use WebDav to update the file… just make sure the file size limits are set high enough in PHP, WP, IIS/Apache, etc to allow the files. You may have to work with the MIME Types and such a bit to get it working…
Good Luck tell me how it goes.
As for #2 you could create a custom field and populate it using the “save_post” action when the file is uploaded.
Similar to “filetype-taxonomy.php” from his “code cookbook”
https://github.com/benbalter/WP-Document-Revisions-Code-Cookbook/blob/master/filetype-taxonomy.php
So:
function wpdr_update_size( $postID ) {
$wpdr = Document_Revisions::$instance;
if ( !$wpdr->verify_post_type( $postID ) )
return;
$post = get_post( $postID );
$attachment = get_post( $post->post_content );
$filesize = filesize(get_attached_file($attachment->ID));
update_post_meta( $postID, 'document_file_size', $filesize );
}
add_action( 'save_post', 'wpdr_update_type', 10, 1 );
If you want to be able to update the value that gets generated, then you will also need to add a custom field. You can do that with a number of free and paid tools outlined within the Document Revisions documentation and by a general Google or WP plugins search.