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Since this is a philosophical debate, I will pose this question to your statement.

I am keeping in mind that "the right thing" is open to interpretation, but even still...
How is allowing Judas Iscariot to commit suicide, doing the right thing?
Surely He was capable of a kind word at the right time to perhaps sooth Judas' tormented soul and perhaps save his life...and his soul?

There are plenty of tough questions for Christians. For some of them there simply are no answers. I guess the only real answer is that faith sometimes goes beyond mere belief in the Trinity, to belief that the Trinity is infalible.

That being said, I don't particularly find excellent questions like yours to be challenging to my faith. I believe that after Jesus second coming when He takes the righteous away with Him, there will be a period of time when the natural questions that need to be answered will be addressed to Him and answered.

Judas did separate himself from Jesus. Had he been listening he would have known that Jesus kingdom was not of this earth. There are some who believe that Judas was trying to force Jesus hand. "If I betray Him He will use His powers to avoid prosecution or death, and He will then assert His authority and set up His kingdom." Judas was wrong. Realizing that he had brought about Jesus death, Judas was crushed.

Judas didn't just doubt Christ, he betrayed Him. He contributed to His death. He missed all the signals. He may have even denied access to the Holy Spirit to the degree that he was without the only direct contact to God that any of us have. Thus, having possibly made the unforgivable sin, Judas may have been beyond rescue.

Jesus was betray and arrested. I doubt anything He could have said would have rescued Judas. The death of Jesus would have left Judas devistated no matter Christ's reassurances.

Hey, this is the best I can do. Like I said, I don't have all the answers. In fact, I have far too few answers.