No, Jesus was slowly making changes to phase out the Old Law. He was making changes in the Law so as to prepare everyone for the New Testament (with his death).
Jesus said,
"Ye have heard that it hath been said, An eye for an eye, and a tooth for a tooth: But I say unto you, That ye resist not evil: but whosoever shall smite thee on thy right cheek, turn to him the other also." (Matthew 5:38-39).
In the Old, the animal sacrifices were required according to the Law, but in the New, Jesus is our sacrifice. Peter was told in a vision to eat unclean animals by God. Peter at first refused because he knew it was contrary to OT Law.
The Scriptures even say there is a "change in the law."
As for Peter and Judas: Well, Peter was later restored for his denial of Christ. Peter had repented of his sin in denying him. Peter did not stay in a rebellious state of denying Christ with the Lord allowing Him to be his disciple.
As for Judas: Well, he was initially saved but then lost at some point in his following of Jesus. No doubt because of his own greed. Jesus doesn't choose evil people to be his disciples. Sorry, that just never happened. That would make the Lord bad and such a thing is not possible.
For what somebody does in the future is different than what they do now. God judges a person in the "present" in real time.
As for Mary: Nowhere is it ever said she continued to be a prostitute while she followed Jesus. That is a false assumption on your part.