Well. this sucks.
The title is correct, but I fucked up in the body of the question, and cannot edit it anymore.
The plugin does exactly 50% of what I would like it to do. It integrates the normal
into the cycle. So with the plugin it now goes
Text → unchecked box → checked box → bullet point → unchecked box → checked box → bullet point → …
However, as I described in the title (and unfortunately not the text itself), every time I hit enter I’d like to be able to go
text → bullet point → unchecked box → checked box → text → bullet point → …
so that one can easily convert something back to normal text again. However, even with the plugin, once you’ve converted away from normal text, you cannot easily revert to it again.