I certainly agree with a lot of what is said here. I wanted to comment on rz1's post.
IMO you have to be careful with the "what if" approach. Do it, but with some reserve. I believe you could push a decision the "wrong" way. By this I mean that I felt that my son was already overwhelmed facing a major decision. We wanted the choice to be his decision and there was more than one offer for him to consider. He was bouncing back between two schools and when he told us he made up his mind, I did not try to place anymore questions. He was confident he could do it.
My son already thought he was in over his head academically. I believe the average ACT in his freshman class was around 30. I am sure that had I pushed or questioned his ability to succeed he would have bailed on the school he is at now, and doing very well I might add.
I always tried to challenge him in every aspect of life and he always lived up to the challenge. The what if analysis is a good part of the process, but don't let that part be an escape route to something he may perceive as an easier route to the same goal.