Tentacle
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Edit images
When cropping an image allow the user to select the area that they would like to crop to. top, left, right... possibly use a jQuery image cropping tool.
Predefined image sizes ( custom post types might use this )
http://www.helenhousandi.com/wordpress/2011/02/showing-other-image-sizes-in-the-media-gallery-dialog/
http://deepliquid.com/projects/Jcrop/demos.php
http://www.phpimageeditor.se/
https://codex.wordpress.org/Class_Reference/WP_Image_Editor