Does he have a well thought out plan to go into Meleches Kodesh such as teaching? or is the only plan to stay in learning as long as possible?
Will all the money that will support his learning be fully Kosher and not cause any diminution Kavod HaTorah?
Will his lack of training to make a living ever create a Nisayon (spiritual test or challenge) for him in monetary matters?
if his plan is to go into teaching, is he willing to take courses that will enhance his ability to teach?