Upload Multiple Images at Once

I agree. I suspect it is not allowed because the site wants to parse the view/preview behaviour for each file independently. This is controlled by the forum platform software so I'm not sure if it will change, but I'll raise the request with them.

i agree. as a workaround i use drag and drop. but that means you don't get to influence the preview size as you do when going through the insert dialogue.

You can click on the image and then choose Edit to have that dialog appear after dragging and dropping:

For images I exclusively copy and paste them in, and then make use of the Edit button starksk is showing in his screen shot.