Hi,

Calvin Young <calvinwyoung@gmail.com> writes:

>    - If the cursor is at the end of a list item, then "Return" should
>    insert a new list item (i.e., automatically perform org-meta-return)

Maybe you can use org-element-at-point and advice org-return?

>    - If the cursor is at the beginning of an empty list item, then "Return"
>    should outdent the list item (or remove it if it's already at the
>    outer-most indentation level)

I don't understand this.  Do you know M-{left,right}?  Again, you could
advice org-return.

In LO it removes the bullet.  Here you can use C-S-Backspace.  Bonus: it
works everywhere!

>    - If the cursor is at the beginning of an empty list item, then
>    "Backspace" should delete the list item and move my cursor to the end of
>    the previous list item

This is like C-S-Backspace C-p C-e.  You could advice org-delete-backward.

>    - It'd be nice of these rules could be applied to checkboxes as well

It should be trivial to support using org-element-at-point.

> What I'm describing is really just the default behavior around bulleted /
> numbered lists in other GUI editors (e.g., Google Docs, Gmail, OSX Notes,
> etc.).

OK...

> Are there any options built in to org-mode that'd let me enable this?

No.  And I doubt it should be.  But Emacs is /your/ extensible editor.

—Rasmus

--
Need more coffee. . .