I've attached a patch which removes the call to skip-blanks if there is no active region.
This works for me with the ECM I've provided.
Not sure if it will have any adverse repercussions outside of that.

>From ada4f2a55b7a701aac02d4fc167be4b46e72f2c9 Mon Sep 17 00:00:00 2001
From: Nicholas Vollmer <iarchivedmywholel...@gmail.com>
Date: Fri, 31 Jul 2020 18:38:11 -0400
Subject: [PATCH] org-list: Operate on single line if no active region

* lisp/org-list.el (org-toggle-item): Operate on single line if no
active region.
---
 lisp/org-list.el | 2 +-
 1 file changed, 1 insertion(+), 1 deletion(-)

diff --git a/lisp/org-list.el b/lisp/org-list.el
index fb061b054..c43630d05 100644
--- a/lisp/org-list.el
+++ b/lisp/org-list.el
@@ -3032,7 +3032,7 @@ With a prefix argument ARG, change the region in a single item."
     (if (org-region-active-p)
 	(setq beg (funcall skip-blanks (region-beginning))
 	      end (copy-marker (region-end)))
-      (setq beg (funcall skip-blanks (point-at-bol))
+      (setq beg (point-at-bol)
 	    end (copy-marker (point-at-eol))))
     ;; Depending on the starting line, choose an action on the text
     ;; between BEG and END.
-- 
2.27.0

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