1. Do the settings in the webassist/ckeditor/contents.css file only control what is displayed in the editor window or what is transfered to the cms content areas?
the webassist/ckeditor/contents.css file only effects what is displayed in the CKEditor window.
the styles in the webassist/ckeditor/contents.css file take precedence in the CKEditor window
you can add style for the h1 and h2 elements to the webassist/ckeditor/contents.css file to change how they appear in the CKEditor Window.