I'm an elected diamond moderator on one site, and a user of several others. I think it would be extremely helpful for our flagging process if users had the option to enter freeform text explaining their flag on types of flags other than the "in need of moderator attention" flag.
An example of when this is relevant: Sometimes posts have had rude/abusive flags, but the rude/abusive part might be difficult to notice, or it might be a single word or sentence buried somewhere in the middle of the post. The nature of the rudeness might also be difficult to recognise for some, especially when it comes to the social issues the Stack is now consciously engaging with. Users have to choose between "flag it as rude with no explanation" or "flag it as misc and explain what's going on". Often users will pick the first because of course it seems like what they should do (e.g. they know the system has special handling attached to rude/abusive flags) but it means they can't explain what's going on to us, so we have to reach out directly in private to find out.
Sometimes it also helps to be able to explain why a comment is no longer needed, because past experience tells me the "no longer needed" flag on its own might be declined on a particular site so I pick the custom reason instead of "no longer needed" just so I can provide explanation.
I'd prefer users be able to understand they can pick the appropriate reason and be able to attach any explanation they deem necessary to further direct moderators to the issue. If not for all kinds of flags, then at least for spam or rude/abusive flags.
