I think it might be better to simply use an "attachment" filearea (similar to forums here, but more compact) rather than embedded links in the HTML and buttons in editors. This is actually what Facebook, G+ etc do.
Future major features
Moodlerooms Proposed Comments User Interface Updates
Agreed. I will update the specification, hopefully by the end of the day with a redesign based on the use of the file attachment for media and the removal of the HTML Editor.
I will also remove the comments tool bar setting in tinymce and the activation of the HTML editor in the commenting settings. I will leave file attachments as a setting for comments and the upload limit as well.