Don't add more automatic messages - the existing ones are being ignored enough
The problem is that the generic text in the boxes that are displayed on your question if it gets put "on hold" can only be that - generic text. There is no way to automatically give precise personalized feedback. The boxes already contain a number of links to helpful resources. For example:
put on hold as unclear what you're asking by <five people> <some time> ago
Please clarify your specific problem or add additional details to highlight exactly what you need. As it's currently written, it’s hard to tell exactly what you're asking. See the How to Ask page for help clarifying this question. If this question can be reworded to fit the rules in the help center, please edit the question.
It's a big box under your question. That's already pretty clear and it takes you to the help center page explaining what this means. Automatic messages can't get much clearer than that.
Try to give personalized feedback when you want to help - especially when voting to close a question from a new user
This being said I think it's the responsibility of everyone who is voting to close a question by a new user to explain why the question should be closed and what this means. At least upvote useful comments already explaining this. If you are voting to close please remember what it was like when you started on the site. There is a lot new users need to learn and it's often quite hidden. Clicking on generic links is also not something everybody always does and reading all this stuff is still pretty confusing at first. We are just different from other forums that people may know.
You can often identify new users based on a quick look at their reputation. Everyone with less than 50 reputation is quite new and probably didn't go through the Ask_On-Hold_Edit_Reopen_Cycle too often. Everyone around ~101 might just have the association bonus and differences between sites can be quite high.
And for everyone: if you see a new users question being put "on hold" please write a comment explaining to them that this is pretty normal here and that their question automatically goes into a reopen review queue if they edit it. This is a process to help increase the quality of questions and to make sure questions conform the guidelines of the site. After that it's always a good idea to give specific feedback, in the best case referring to previous comments about what could be done better.
And also try to give feedback when not voting to close but suspecting others might want to close it
When seeing a question that is likely to be closed, for example because someone is asking about how something would affect society, please write a Welcome to WorldBuilding comment explaining what is wrong and link to useful resources. A specific comment with real advice towards the concrete question will always be far more useful for everyone than generic canned comments.
There is already a lot done through automatic messages. But it requires users to read obviously generic messages and people don't do that because they assume they won't get specific advise that might help them - which of course is true. So everyone reading this - please try to be a rolemodel when it comes to new users and guide them with specific feedback and links to the resources that are really important for the specific case you are reviewing - whether it's in one of the formal review queues or just because you came across the post through browsing the site.
