Some new users struggle to write a good question first time around. We already help in comments (e.g. by linking to helpful resources) but this does not always result in the question being improved to the point where it can be reopened.
One possible cause for this is that the Q & A format is simply too different for users to grasp without one-on-one assistance. For example, markdown formatting and sample data generation/presentation can be quite challenging if you have never used a Stack Exchange site before.
This can all be much more challenging where English is not the user's first language, since all the help available is written in English. Not all Help Center entries are a model of clarity either.
Experienced users would invite the new user to chat to help improve their question.
This would involve moderator assistance (via a custom flag), because new users cannot talk in chat until they reach 20 rep. (The normal mechanism of auto-copying long comment discussions to chat does not work either, and is too slow in any case.)
We would place the question on hold while the improvement process takes place.
If the author does not wish to take part, or the question is not sufficiently improved for any reason, the question would transition to closure and be deleted as normal.
Is this a good idea?
Are there any experienced users willing to help in this way?
Would a single dedicated chat room or a chat room per question be better?
Any other feedback?
To be clear: this is a specific proposal for something we could do now, without waiting for any site development work, which is currently in a queue 6-8 years long. It won't solve all problems with the new user experience, but it might just not make them any worse, or even help a tiny bit.