Thanks for the response. I think a section like the “Select specific images (optional)” pane would be perfect. Certain images could be selected and have the URL appended, eg:
batman.jpg=www.worldofbatman.com
enterprise.jpg=www.startrek.com
So when those images are displayed, they are clickable.
100 images? Well the user specifies a URI in the “Path to images” text box of your widget config. You could present a two column list where each row consists of [image-name or image-preview][URL (empty by default, user provided)]. This might be a better solution. Since the Hot Random Image widget config is in a collapsed entry in the Blog Sidebar it wouldn’t take up any screen space until the user decides to got there.