Hello,

On master (commit: 51b339105), attempting to convert a blank 
headline to an item with `org-ctrl-c-minus' removes the space 
after the * and org no longer recognizes it as a heading. 

I believe this issue originated in commit 69c5b6c99. Some code was 
added to strip metadata during the conversion in `org-toggle-item' 
with `org-heading-delete-metadata'. '(org-set-tags-to nil)' is 
used to strip tags which in the case of the blank heading results 
in `(delete-region (match-beginning 1) (match-end 1))' being 
called.

`delete-region' in this case removes the space immediately after 
the star/s in the blank headline which puts the line in a state 
that org doesn't consider a headline.

Replacing the removed space following the * or preventing its 
removal would remedy the issue, but I wasn't sure where to 
implement this. Didn't want to make the change in 
`org-set-tags-to' for fear of downstream effects.

Cheers,

-- 
Adrian

Bioelectronic Systems Lab,
Columbia University