1. You can right click on the image and choose "Image Map Editor" . The Image Map Editor has a property "Target" which you can use.
2. Out of the box this is not supported. The could be done with a custom code where you get the selected HTML
and send it to the selector. You should modify insertLink() of Sitefinity\Admin\ControlTemplates\Libraries\Dialogs\DocumentEditorDialog.ascx where we set the document text.
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