Portland ME - One feature Drupal has always been missing is a robust media management system. For all the reasons I dislike Wordpress, in my opinion has the best media management. Drag and drop file uploads and an intuitive editing browser that includes caption editing, image size manipulation and rotation make it my favorite. However my Drupal family is making progress.
The Media module is the go to for giving users the ability to manage their media. It's solid and does a descent job but it is missing drag and drop upload, multi-select and the slick editing features that are included in Wordpress. But we are getting closer. If you are reading this post at the time of the writing a small patch is necessary but drag/drop and multi-select are now possible. Due to some jQuery conflicts, get the 7.x-2.x-dev version of the Media module. Then download the Plupload Integration and its library. Lastly you need to get this patch. This amazing patch includes work to allow Plupload to work inside the Media Browser for drag and drop multi-upload and multi-select.
If you are reading this post after the date posted, check to see if the patch has been included in a release. What I am most happy about is all things necessary to improve the Media module's functionality are being done inside the project as opposed to multiple other modules.