>The file chooser issue is more often raised in the context of internet abuse than good faith user requests
What are you basing this on? That sounds incredibly dismissive. I think the core of the issue is that you're so out of touch with your users, that you're mistaking a highly requested feature with hostility. Maybe a user survey would be a good idea to bridge the gap.
I think one large discrepancy is that this only affects a subset of users who frequently handle a large amount of images. In this example, it is users of image boards. But it also includes artist, photographers, etc. Not so much professional programmers. But to those who are affected, they are hindered greatly.
I also see an issue with your idea that there are "good faith" and "bad faith" feature requests. This seems like a really unhealthy way to look at things. There is no conspiracy that there are a bunch of people out there that want to give you a bunch of work to do just to mess with you. 100% of these people are honestly affected by the issue and would like it resolved.