0

My checkbox list appears as shown below
checkbox list right now

I would like to have it like this.
checkbox list as desired

As you can see the number of digits for the numbered list is two, starting at 01.

I do not see an opportunity where we might need 001, so 01 should be good.

2

The following modifications allow bullets with leading zeros in org-mode version 8.3.6:

--- ~/.emacs.d/elpa/org-20160425/org-list.el    Sun May  1 10:12:55 2016
+++ /tmp/org-list.el    Tue Oct 25 22:49:47 2016
@@ -367,6 +367,14 @@
      (list (symbol :tag "Major mode")
        (string :tag "Format"))))

+(defcustom org-list-keep-leading-zeros t
+  "Keep leading zeros in numeric list bullets, i.e.:
+ 01. [X]
+ 02. [X]"
+  :group 'org-plain-lists
+  :type 'boolean)
+
+
 (defvar org-list-forbidden-blocks '("example" "verse" "src" "ascii" "beamer"
                    "html" "latex" "odt")
   "Names of blocks where lists are not allowed.
@@ -1656,10 +1664,13 @@
   (let ((case-fold-search nil))
     (cond
      ;; Num bullet: increment it.
-     ((string-match "[0-9]+" bullet)
-      (replace-match
-       (number-to-string (1+ (string-to-number (match-string 0 bullet))))
-       nil nil bullet))
+     ((string-match "\\([0]*\\)\\([1-9][0-9]*\\)" bullet)
+      (replace-match (format 
+             (if (match-string 1 bullet)
+             (concat "%0" (number-to-string (length (match-string 0 bullet))) "d")
+           "%d")
+             (1+ (string-to-number (match-string 2 bullet))))
+            nil nil bullet))
      ;; Alpha bullet: increment it.
      ((string-match "[A-Za-z]" bullet)
       (replace-match
@@ -1731,7 +1742,12 @@
         ((and alphap (string-match "[a-z]" bullet))
          (replace-match "a" nil nil bullet))
         ;; First bullet is num: use "1".
-        ((string-match "\\([0-9]+\\|[A-Za-z]\\)" bullet)
+        ((string-match (concat "\\("
+                   (if org-list-keep-leading-zeros
+                       "[1-9][0-9]+"
+                     "[0-9]+")
+                   "\\|[A-Za-z]\\)")
+               bullet)
          (replace-match "1" nil nil bullet))
         ;; Not an ordered list: keep bullet.
         (t bullet)))))))))

The relevant code which you can use to override the org-mode definitions is:

(defcustom org-list-keep-leading-zeros t
  "Keep leading zeros in numeric list bullets, i.e.:
 01. [X]
 02. [X]"
  :group 'org-plain-lists
  :type 'boolean)

(defun org-list-inc-bullet-maybe (bullet)
  "Increment BULLET if applicable."
  (let ((case-fold-search nil))
    (cond
     ;; Num bullet: increment it.
     ((string-match "\\([0]*\\)\\([1-9][0-9]*\\)" bullet)
      (replace-match (format 
              (if (match-string 1 bullet)
              (concat "%0" (number-to-string (length (match-string 0 bullet))) "d")
            "%d")
              (1+ (string-to-number (match-string 2 bullet))))
             nil nil bullet))
     ;; Alpha bullet: increment it.
     ((string-match "[A-Za-z]" bullet)
      (replace-match
       (char-to-string (1+ (string-to-char (match-string 0 bullet))))
       nil nil bullet))
     ;; Unordered bullet: leave it.
     (t bullet))))

(defun org-list-struct-fix-bul (struct prevs)
  "Verify and correct bullets in STRUCT.
PREVS is the alist of previous items, as returned by
`org-list-prevs-alist'.

This function modifies STRUCT."
  (let ((case-fold-search nil)
    (fix-bul
     (function
      ;; Set bullet of ITEM in STRUCT, depending on the type of
      ;; first item of the list, the previous bullet and counter
      ;; if any.
      (lambda (item)
        (let* ((prev (org-list-get-prev-item item struct prevs))
           (prev-bul (and prev (org-list-get-bullet prev struct)))
           (counter (org-list-get-counter item struct))
           (bullet (org-list-get-bullet item struct))
           (alphap (and (not prev)
                (org-list-use-alpha-bul-p item struct prevs))))
          (org-list-set-bullet
           item struct
           (org-list-bullet-string
        (cond
         ;; Alpha counter in alpha list: use counter.
         ((and prev counter
               (string-match "[a-zA-Z]" counter)
               (string-match "[a-zA-Z]" prev-bul))
          ;; Use cond to be sure `string-match' is used in
          ;; both cases.
          (let ((real-count
             (cond
              ((string-match "[a-z]" prev-bul) (downcase counter))
              ((string-match "[A-Z]" prev-bul) (upcase counter)))))
            (replace-match real-count nil nil prev-bul)))
         ;; Num counter in a num list: use counter.
         ((and prev counter
               (string-match "[0-9]+" counter)
               (string-match "[0-9]+" prev-bul))
          (replace-match counter nil nil prev-bul))
         ;; No counter: increase, if needed, previous bullet.
         (prev
          (org-list-inc-bullet-maybe (org-list-get-bullet prev struct)))
         ;; Alpha counter at first item: use counter.
         ((and counter (org-list-use-alpha-bul-p item struct prevs)
               (string-match "[A-Za-z]" counter)
               (string-match "[A-Za-z]" bullet))
          (let ((real-count
             (cond
              ((string-match "[a-z]" bullet) (downcase counter))
              ((string-match "[A-Z]" bullet) (upcase counter)))))
            (replace-match real-count nil nil bullet)))
         ;; Num counter at first item: use counter.
         ((and counter
               (string-match "[0-9]+" counter)
               (string-match "[0-9]+" bullet))
          (replace-match counter nil nil bullet))
         ;; First bullet is alpha uppercase: use "A".
         ((and alphap (string-match "[A-Z]" bullet))
          (replace-match "A" nil nil bullet))
         ;; First bullet is alpha lowercase: use "a".
         ((and alphap (string-match "[a-z]" bullet))
          (replace-match "a" nil nil bullet))
         ;; First bullet is num: use "1".
         ((string-match (concat "\\("
                    (if org-list-keep-leading-zeros
                        "[1-9][0-9]+"
                      "[0-9]+")
                    "\\|[A-Za-z]\\)")
                bullet)
          (replace-match "1" nil nil bullet))
         ;; Not an ordered list: keep bullet.
         (t bullet)))))))))
    (mapc fix-bul (mapcar #'car struct))))

Install this code in your init-file -- maybe after (require 'org-list). Afterwards, you can insert your first bullet with the right number of zeros at the front and all other bullets are formatted accordinly by keystrokes like C-c C-c or M-return

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