Customizing the menu this way is as for as I can tell, not very friendly. What I had to do recently was custom built the submenu item using remove_submenu_page for all the sub menu items and then add them in the order I wanted using add_submenu_page.
A simple example
//this was first sub-menu item I did not want it #1
remove_submenu_page( 'edit.php?post_type=test', 'edit.php?post_type=test' );
// add the actual sub-menu item I wanted as #1
add_submenu_page('edit.php?post_type=hello','Hello', 'Hello', 'manage_options', 'my_hello', 'my_hello_options');
//re-add the orginal #1 item removed above so it is now the #2 item
add_submenu_page('edit.php?post_type=test','Edit Test', 'Edit Test', 'manage_options', 'edit.php?post_type=test');