Jesus - undercover agent?

Matthew 8:1-4

I have no idea in which region Jesus preaches his sermon from the mountain. The verses just before that say that large crowds from Galilee, the Decapolis, Jerusalem, Judea and the region across the Jordan followed Jesus. Where ever the sermon takes place, Jesus comes down from the mountain and begins to heal people.
There are two things that I don't understand:
1) Why did Jesus tell people that he healed not to tell other people what happened? I mean, there were large crowds following him anyway so it isn't like this healing was going to be kept secret. Also, most of the people he healed didn't obey this command anyway and went around spreading the news about what happened to them. Finally, doesn't Jesus want people to know that he has authourity over disease, demons and death, proving that he is the Messiah? Was Jesus just using reverse psychology, recognizing that human nature loves to know something others don't and to be the one that tells others? If that is the case, then it seems a bit manipulative of Jesus.
It could relate to his temptations. Jesus was tempted to use his power to survive a jump off the temple which would certainly draw people to him and make a name for himself. Jesus would realize that his healings, while necessary to demonstrate his authourity, would also be seen to be spectacular and that people would come to see him as simply a miracle worker, as cheap entertainment. They would be drawn to him because of his tricks and as long as he kept doing tricks for them, they would be loyal to him. Related to that, he may have wanted people to truly come to discover who he was for themselves, not based on a rumour of a healing that was done. This would allow people to discover that he was more than just a "one trick pony" - that his main agenda was compassion, grace, love and sacrifice.
Secondly, I wonder why Jesus supported the tradition of the Law when it came to this healing. He told the leper to follow the ceremonial requirements for being made clean: go and show himself to the priest and make the necessary sacrifices. This is a puzzle to me because a main part of Jesus' message was the end of these religious practices. It would seem like a good opportunity to tell the people that they don't need to observe the burdensome practices of ceremonial law in order to be reconciled to God.
I wonder if something else was at stake here though. I wonder if Jesus told this man to observe the ceremonial requirements in order to be accepted back into community. As a leper, this man was untouchable and was an outcast from society. I wonder if Jesus recognized that for this man to be re-integrated back into society that he needed the official declaration from the priest that he was now clean. This would make sense, especially in light of Jesus' message in his just preached sermon: to treat everyone with the dignity, honour and respect they deserve as a person created in the image of God. Jesus was showing great respect to this man in, first of all, touching the man and then providing a way for him to be embraced again by his family and friends.
What's the lesson for me? I think that first of all I must be willing to be seen as unclean because of the people that I associate with and embrace. I must be willing to take the same risks socially that Jesus took. Who are the untouchables in our society and who is showing them the compassion, dignity, honour and respect that God wants to communicate to them. Second, I think I need discernment to know when to buck the system and when to work with in it. When the system provides a mechanism for helping someone regain their dignity, then I must be willing to at least consider working with in it. Even if it is the same system that stripped the person of their dignity in the first place.