I agree: unless it's something outright malicious or otherwise similarly extreme (such as NSFW images or blatant copyright breaches), it's probably not worth the hassle to remove.
I have two old uploaded files from 2012 that are outright unusable gibberish because I didn't know about the restrictions on file names. (I have no idea whether they even take up any space on the server.) I still don't bother with asking anyone to remove it, because it's still not worth the hassle.