Yes, prayer must be a part of discernment, I agree. I think your comments are very insightful. I'm not sure about the grey areas that you speak of however. I am talking about the "rules" of Jesus Christ, not the laws of the world. I guess you said "world of laws", so maybe you mean, like in todays Gospel reading, Mark 2:23-28, quoting verse 27 "the sabbath is made for man, not man for the sabbath" like the pharisees and their hypocrisy. But if you are following the "rules" that God puts forth; the ten commandments, the church as defined in the catechism, the sacraments, the magisterium, sacred scripture, you are going to be on the right track. I guess I think of the love of Christ in His "rules", which our prayer life should coincide with, if properly ordered. Christ calls us out of our sin and weakness, into a life of grace, by His teachings and with His mercy. He asks us to be perfect, as His heavenly father is perfect, Matthew 5:48. Even if I may never be perfect in this life, I can slowly approach it, by always growing in the body of Christ, in the grace He provides for my repentant heart. One way this could be measured is by my confessions, as I should be sinning less, and praying more if I truly mean to follow Him, since as I grow in grace I learn to choose Christ, and be "obediant". It's not always easy to discern a given decision or course of action, if that is what you mean. I like what Lauren has written also.
Yes, David I was speaking of just equating obedience with the following of laws - which is part of it, but not the full picture. I've sinced realized that obedience also has to do with listening to God through prayer, taking the doctrines that our Church teaches and applying them to the decisions I make in life to the best of my ability and understanding. Rather than seeing my relationship with Jesus only in terms of my juridical status (am I following everything He said) I also realize the dynamic response to Him through my decisions based on the TRUTH of His teachings.