Not sure if it's a bug or not, but IIRC adding any opening or closing tags between list elements will result in problems with inline editing on that first post. The post will still edit, but the rest of the javascript fails to run (re-adding the post and removing the loading indicator). Has that been fixed (I'm still on an old version)?
This request requires further discussion, because you can not insert something other than an <li> between messages, and the system expects that each <li> represents a message.