You said: “Sin is offensive to God, but its consequences are not.”
I reply: Sin is offensive because it causes suffering and death. God is good and he can only desire which is good for us.
'… Even though man’s nature is mortal, God had destined him not to die. Death was therefore contrary to the plans of God the Creator and entered the world as a consequence of sin. Bodily death, from which man would have been immune had he not sinned is thus the last enemy of man left to be conquered.” (Catechism of the Catholic Church, 1008)
“Sin offends God, that is, it saddens him greatly, but only in so far as it brings death to man whom he loves; it wounds his love.
.” (Fr. Cantalamessa, Life in Christ: The Spiritual Message of the Letter to the Romans)
You said: "The choice of a demon to possess a man is offensive to God, but the possession is not necessarily (for he casts out demons when he becomes weary of them possessing man). "
I reply: God is offended by all suffering and death. This includes demon possession. He cast them out only through us. If no one prays they will not be cast out.
You said: "If it were an evil of God to strip away the effects of free will,
I reply: Because it would diminish other gifts given to us.
You said: that is, the consequences of sin, e.g. demonic possession, then Jesus would have been committing evil in obstructing the demon’s will to possess a man. But Jesus did cast out a demon."
I reply: The explanation is that God cannot intervene in the world because it would diminish our gifts The demon can have his will but Jesus in acting in a finite capacity can cast out demons with his gifts. The explanation goes as follows:
"In the incarnation, God assumes a created human nature, and acts with finite powers that are proper to man. As a necessary aspect of the incarnation, God begins to act within the world according to the normal and limited sphere of influence that would be given to a human being as part of the created order. We therefore see a singular exception to the prohibition of direct divine intervention in terms of finite affairs.
As true God and true man, Jesus performed miraculous healings and exorcisms within the finite human capacity that was appropriate to him according to created human nature. He healed those who came to him as a sign that he had come to bring justice to the world. He showed, through every action, that suffering and death were enemies to be defeated, and that he has come to bring justice to the world by delivering man from the power of evil.
This power of healing has not left the world.
In remaining consistent with the principle of giving all that can be given, after his ascension, through the coming of the Holy Spirit, Jesus entrusted his human ministry of healing and deliverance to his Church, most particularly to the apostles and their successors, the bishops. As with any other power given by God, it is truly given, and it is presently in the hands of the Church. If this gift is not taken seriously, then there are consequences for the whole world because of the omission. In the same way that a lack of teaching and preaching has its effect on the world, so it is that a lack of prayer for miraculous healing will cause many people to suffer unnecessarily." New Apologetics
You said: " If Jesus wanted all who were afflicted with demons to be freed, why should he not, then, cast out the demons? Why did he cast it out of some but not others? Does our Lord will good on some and not others? But of course he loves us all, and so leaving some possessed and others freed, he must see some ultimate benefit, that he allows evil to run its course."
I reply: He does want all demons to be cast out. The gifts is in the hands of the Church. Jesus cast out demons from every person he came across. When a demon(s) are not cast out it has to do with how strong the demons are and how many. It also has to do with:
“Because of omissions within the Church (i.e. the sins of Christians), the lives of even those who are obedient to Christ’s call to heal the sick and preach the gospel are reduced in their efficacy because they are not upheld by the gifts of the others who would be acting in conjunction with them throughout the world by lives of prayer and sacrifice. Because of the unity of humanity, when one member of the Church is not living a holy life, all are affected in a negative way correspondingly. As more individuals within the Church begin to live under the power of the Holy Spirit, then the ministries of healing and preaching will begin to reflect the same power of the ministry of Jesus himself.” New Apologetics
You said: Let’s talk about Job. Satan doesn’t go off and harass Job, but God grants him permission and tells him exactly what he may do. God assures us that no temptation will be too great for us. If the free will of man led to consequences for mankind that were beyond the scope of God’s power, then God would not be able to say “no temptation shall be too strong.” For the only reason it is not too strong, is that God prevents it from overwhelming us. When we are tempted, it is his good pleasure, for he sits refining his silver. We are scorched in the furnace until we are perfected. Not a moment too long do we sit in the furnace, but he knows exactly what is best for us
I reply: The bible is progressive revelation. People were gradually coming to know of who God is and he is love. The book of Job is not a literal theological teaching on God. Woe to us if it was!
“God is infinitely good and all his works are good. Yet no one can escape the experience of suffering… We must therefore approach the question of the origin of evil by fixing the eyes of our faith on him who alone is its conqueror.” (Catechism of the Catholic Church, 385)