Discussion
When M-S-RET is one key press too much: M-RET to the rescue!
While M-S-RET is totally fine to insert list items with a checkbox I find myself often in a situation where I press M-RET and only afterwards recognize that I forgot the S part. Then I have to delete the new line and insert a new one this time really using M-S-RET.
Below advice helps me getting new list items with checkboxes even when only using M-RET to insert a new one.
(defun org-insert-item-advice (origfunc &optional checkbox)
"An :around advice for org-insert-item.
Will automagically insert a checkbox for a new item if current item has one."
(let* ((itemp (org-in-item-p))
;; check if cursor isn't in a list or if list is invisible
(notinlist (or (not itemp)
(save-excursion
(goto-char itemp)
(org-invisible-p))))
(cb (unless notinlist
(save-excursion
(goto-char itemp)
(if (and (looking-at org-list-full-item-re)
(match-string 3))
'cb))))
(checkbox (or checkbox cb)))
(apply origfunc (list checkbox))))
(advice-add 'org-insert-item :around #'org-insert-item-advice)
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