The idea is to sort Images in views from lowest to the highest quality (not only size).
Image A = 640x480 100ko (blurred darkened)
Image B = 480x320 50ko (detailed)
1 - Image B
2 - Image A
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The only way that I see is calculate image quality when it's saving and use it later. How to do it:
How to calculate image quality? Here is good example but you can use your own approach to do it.
P.S. Yes it looks a little tricky but I don't think that it's possible to do it easier. But if it's possible I'll be happy to hear it.
The easiest, but most time consuming, would be to create tags via taxonomy.
Views supports taxonomy filtering and sorting really well. The reason this is a lot of work is it will require manual tagging.