The issue with hotlinking is that we need the ability to control the content that appears on our website. If laws change, and they sometimes do, I don't want to have to manually review thousands of forum posts to look for images that are hotlinked from somewhere else.
This might be a strange question, but would it be possible to allow replacing pictures that you've uploaded? Say you have found a better resolution version of an image, or perhaps you decided to shrink it to better fit on the forum. If you upload a picture with the same filename to replace the old one it will still have a different link on the forum. And then you have to manually edit all posts where its used (and its practically impossible to find those).
It kind of seems like the risk that overwriting some filename like "hotcover.jpg" or "screenshot7.jpg" whatever name would outweigh the convenience of what you are talking about. But what do I know?
Depends on how you do it. There could be a "replace" button next to the image which would practically prohibit errors. Or there could be a warning with two options if you upload something with the same file name. Or something else that I haven't thought of.
I assign random filenames to store uploaded files on the drive. The filenames don't match the image name in URLs so there's a lookup that associates the URL with the name stored on the drive. I'd make the swap at that relationship point. So it's not really an overwrite, more of a replacement.