That would be a great idea, I wonder how the plugin would deal with that though? Would it keep the same dimensions but compress the image more aggressively to get it under the size limit? Or would it just keep minimizing the dimensions until it fit the size limit..? I think the plugin would have to be a lot more intelligent to do that and would have to make decisions about the how to decrease the size.
I think it should always keep the same dimensions but, as you say, compress the image more aggressively. Its then down to the Administrator to test the quality of the images before applying the plugin permanently. I maintain a website for an art school and students like to upload images that are sometimes 5MB plus. If I could limit the size of the images to 500KB then I think this would still give you an acceptable quality.
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