With numbering you can do something like this where you find the last element of the previous list, and then continue it. This won't do what you want for nested lists I guess. For lettering, you would need to figure out how to increment the letter. but for simple numbered lists, this might do the trick for you.

#+BEGIN_SRC emacs-lisp
(defun auto-continue ()
  (interactive)
  (when-let (p (org-in-item-p))
    (save-excursion
      (goto-char (line-end-position))
      (goto-char (org-element-property :contents-begin (org-element-context)))
      (let* ((lists (org-element-map (org-element-parse-buffer) 'plain-list
     (lambda (lst)
(when (eq 'ordered (org-element-property :type lst))
 (cons
  (org-element-property :end lst)
  (length (org-element-property :structure lst)))))))
    (last-list (nth (- (or (-find-index (lambda (x)
  (> (car x) (point)))
lists)
   (length lists))
1)
    lists)))
(insert (format "[@%s] " (+ 1 (cdr last-list))))
(org-ctrl-c-ctrl-c)))))

#+END_SRC