You want to be able to sort them in the post? What's stopping you from rearranging them in the post content?
Allow sending images in direct messages
I use the direct message feature a lot in my own forum, however I feel that it is lacking a pretty normal feature, uploading images in direct messages. I believe that they would be used much more and would serve more of a purpose, as currently you can only send text.
This will be available in 1.19.2, will also allow drag drop in the quick reply box in persona