Regarding the behavior of org-insert-todo-heading-respect-content, bound to C-S-return, consider the following .org file:
* TODO some task ** WAITING other task If point is on the TODO line, pressing C-S-return yields * TODO some task ** WAITING other task * WAITING When I use C-S-return, I always desire * TODO some task ** WAITING other task * TODO Making C-S-return do this would break backward compatibility, but I think this behavior is more intuitive. Thoughts?