kraftner, 
If you ask me media handling in #WordPress is currently utterly broken:
- generating image sizes only on upload
- no proper way to (re-)generate thumbs (incl. show-stopping bugs in WP-CLI)
- no media usage tracking
- orphaned files on editing images
- no folders/structuring in the backend
- incomplete/manual responsive image size handling (not even talking about content-awareness or art direction)
I know there are plugins out there but that itself is really weird for such a core feature.sigh
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