New SS user here and discovered not being able to directly delete images in My Library. Even if the images are hosted on a third party to speed up loading of images, as one has suggested, it is not an excuse to not have this feature or improve on what is occurring.
Search Help section with the phrase "Image and file URLs in Squarespace" to find details on what has been discussed on this thread.
One thing, SS can do is require the CDNs to shorten the time it takes to purge the images/files. Instead of it taking 7 days, or 30 days, why not require them to remove it sooner?
Keep in mind when uploading images, if someone knows how to find the URL to the image (which is described in the above mentioned Help article), they can have extended access to that image until it's finally scrubbed 30 or so days later, even if you "delete it" or don't publicly display it your site.
