How can I configure the backend to get a comfortable image insert functionality with captions? Since Drupal offers many different approaches to inserting images, I am a bit lost. I am looking for a configuration that allows editors to comfortably insert images with captions. My requirements are:


Works with WYSIWYG editors
One input form to upload the image and enter the caption
At most one more step in the workflow to position the image in the text
Ability to create blocks with several images side-by-side
Ideally, no code changes (inserting JavaScript or altering PHP) should be necessary in order to retain upgrade capabilities


It seems that many people are using a combination of the wysiwyg module with IMCE and the IMCE wysiwyg bridge. However, I don't see any support for image captions in that toolchain. 

The other alternative is the Insert Image With Text module, which is still in beta and rarely discussed anywhere. As far as I understand, this method is not really practical because it limits users to one image per node (or would require several image fields in the respective content type).

Is there any combination of modules and content settings that can fulfil those requirements?
Have you tried the Media module? From the project page: 


Add media (images and video) into any textarea (requires Wysiwyg module).
Use the fields API (formerly CCK) to add fields to any type of media, eg. captions on images.
Plugins to use remote media from sites like YouTube, Flickr, ...
A unified interface for adding any type of media as a field to nodes.
Mass importing of files.
Drag and drop upload (with Plupload module).
Responsive image support (with Picture module).