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I just tested on core. In works to drag/drop the images in wp-admin to confirm the order. Featured Image is always first (and in case you have a video too – the featured image is replaced by the video). This is for small slider only.
This screenshot may help http://help.wpestatetheme.org/assets/images/upload2.png
If you still can’t make it work, please send me wp-admin credentials and I’ll do a test on your domain directly ([email protected])