Bro James let me answer these questions in two phases.
The first thing was that the chief priest had to send in soldiers that may never have paid attention to Jesus too. And more so considering that most of the men in those days wrapped their heads it could be difficult to identify Jesus from his disciples. That is why there was need for a close identification like the kiss.
Perhaps it was divine ordination. It could always be that God had already assigned him for perdition in terms of predestination. But if that was the case he should not have held him responsible. Yet the problem that caused Judas to do what he did was his hyperopia (langa) for money. That is why he took the 30 pieces of silver. But when he realized his mistake he decided to go and return the money (Mt 27:2-5). The immediate question that arises is why then did Jesus not forgive Judas? As you read through the passage it states that Judas felt sorry for his sin but he did not repent or ask for forgiveness. He would have gone to the master he had access too and tell Him master I did you wring, please forgive me and restore me into the fellowship. Rather he wanted to take care of business his own way. When the people rejected the return, Judas dropped the money in front of them and went and committed suicide. His suicide has raised some objections because in Mat 27: 5 it says but in Acts 1:18 it says he.
There were two ways of hanging. One was by crucifixion while the other was by falling headlong on a goad or a tree stump. Luke who is the author of Acts as a gentile wants to make the specifics and details to every one but Matthew a Jew does not see the importance to be narrating the details which they were ashamed of.
The second seeming contradiction is when Matthew says the chief priest used the money to buy a piece of land while Luke says in Acts that he (Judas Iscariot ) used the money to buy a piece of Land. Luke uses a principle of ownership called the power of delegation while Matthew presents the ownership by virtue. According to Luke, Judas bought the land because the money was Judas’ the land will be registered in his name. According to Matthew, though it was Judas’ money but the chief priest used the money therefore they too should be held accountable for failing to protect their own and instead betraying him. That is why he presents the story to show the culpability of the chief priests too.
One reason why it needed people to find Jesus is that from the time they wanted to kill him by throwing him into the pit (Lk 4:28-29) from that time he has been living his life moving from one city to another and making himself difficult to find and when they found him he was in the temple and if the religious leaders try to hurt him in the temple the people will question their commitment to the cause of God. So it was difficult to find him and because of this it needed an insider to betray him. That is where the traitor comes in. Judas was the turncoat out of money desires because remember he has been stealing the money in the coffers of the ministry.
Jesus knew ab initio that Judas was a devil (Jn 6:70) but he still selected him perhaps to give him the opportunity to turn away from sin. He did not care for the poor but he cared for the money especially because he kept the money bag from which he could pilfer (Jn 12:4-6). Living perpetually in sin he has been possessed by Satan (Jn 13:27) that he could no more come back to Jesus for repentance and ablution.
Until then, enjoy.
Prince & PA Hamilton Ayuk