All right, I'll jump in. I understand that the other 48 guys who have access to post on this blog are busy. Whereas Greg, Mike the spiteful Brit, and I seem to have unlimited time.
With respect to #2, I think the way forward is to shoot straight with your brother. If you haven't been fruitful in ministry before you sensed a call, you probably won't suddenly become fruitful just becuase you have a seminary degree or a paid position in a church.
It's also worth investigating why your friend wants to pursue ministry. Most of us don't pursue opportunities to do things that we're not good at (me and my blogging career aside).
1. Does he have an inflated sense of his gifts and fruitfulness? If so, you may have to go to the tape. "Brother, you're a horrendous preacher. Please don't ever do it again under any circumstances." (or something roughly to that effect) may be the nicest thing anyone ever says to him.
2. Does he feel unwarranted guilt over not serving in full-time vocational ministry, as if those who really want to be excellent Christians need to be in paid ministry? If so, it may be helpful to instruct him on vocation.
But, with all that being said, it could be that you're wrong and God plans to do crazy things for the kingdom through this guy. So you've got to approach it with humility and love for your brother.