Indeed, sometimes when adding non-box-oriented content as inline editable, the wrapping editor has troubles identifying them.
For example you can’t have a floating image content next to a paragraph content, unless you use a new custom node type that does exactly that (ie
Neos.NodeTypes:TextWithImage). If you try to do it with Image node type in combination with Text node type, you will be unable to select the image from inline.
I had this problem with various use cases, some of them were better with a workaround, but in some of them I would prefer a smarter content selector.
I think a nice solution to this problem would be to change the selected content wrapper if the user clicks again on the already selected wrapper, but that’s going to be tricky since the click event fires only on the element on top of the z-index.