Personally, I love everything about Drupal 7 except for the file upload / WYSIWYG process. I really like the core image upload but not any WYSIWYG upload system. I also like the fact that they are separate (allows for more customization).
When a file is uploaded using the WYSIWYG editor, you are given the option to either select an image already uploaded or an image from your computer. However, when an image is uploaded from within the Editor, an new path is not created based on a pathauto/token system like the core uploader.
Would it be possible to create a module that uses the core upload module, but also creates a 'shortcode' that one can use to place that image inside the body??
The path I would like all image uploads to abide by would be something like:
files/[year]/[month]/
Example:
Lorem ipsum dolor sit amet, consectetur adipisicing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam, quis nostrud exercitation ullamco laboris nisi ut aliquip ex ea commodo consequat.
[shortcode:image_1:thumb]
Duis aute irure dolor in reprehenderit in voluptate velit esse cillum dolore eu fugiat nulla pariatur. Excepteur sint occaecat cupidatat non proident, sunt in culpa qui officia deserunt mollit anim id est laborum.