Drupal is a extremely powerful tool but we’ve all had to deal with some fair criticisms regarding user experience. Some of them are being addressed in Drupal 8 and others with the help of contrib modules.
When it comes to file management, Media module provides us a number of features that make it almost mandatory for any Drupal project.
However, when we’re dealing with content types with a lot of image files, editing a node may become somewhat cumbersome. Fortunately there are a number of modules that extend Media core framework features.
Mediadesk allows you through the 'Media Desk Selector' widget to set a field for central management of images , where you can upload or select those that you wanna use on the node edit form and from there drag & drop them on all the image fields (as long as they use use 'Media Desk image' widget).
If set up with Plupload you’ll also have the change to upload multiple files at once (via drag & drop or from the browser dialog)
and with Manualcrop, you get image cropping through the image editing interface.
Give it a try and see how it fits in some of your projects. We’re quite happy with this current setup.