Judas and Repentance

The wonderful medieval hagiography "The Voyage of St. Brendan" has an amazing account of how right before they reach paradise, they find a rock in the middle of the stormy sea, and on it sits Judas Iscariot the betrayer. He explains that this is his vacation from Hell which God mercifully allows him on good friday each year (I think I got it right, but I'm working from memory).

Matthew 27:3-5
"When Judas, his betrayer, saw that Jesus was condemned, he repented and brought back the thirty pieces of silver to the chief priests and the elders. He said, ‘I have sinned by betraying innocent blood.’ But they said, ‘What is that to us? See to it yourself.’ Throwing down the pieces of silver in the temple, he departed; and he went and hanged himself."

From a Thomistic/Catholic perspective, Judas had everything necessary. He was contrite, he confessed, and he rendered satisfaction and reparations. There was really nothing lacking (though one might argue he should've gone to Peter or another apostle, as he confessed to 'outside' authorities).

I've been trying to understand the story and have always at least known that he Judas was probably sent to Hell for suicide if nothing else. However his betrayal of Christ is always seen as the main reason for his guilt (even though other gospels say it was Satan in him).

Fr. Timothy Radcliffe O.P. seems hopeful that Judas will make it to heaven, and others have echoed his sentiment. I went to the Fathers for their commentaries and found some interesting stuff.

Pope St. Leo the Great writes:
"When he says, I have sinned, in that I have betrayed innocent blood, he persists in his wicked treachery, seeing that amid the last struggles of death he believed not Jesus to be the Son of God, but merely man of our rank; for had he not thus denied His omnipotence, he would have obtained His mercy."

Origen also has an illuminating commentary:

"...sorrow being made too abundant might swallow up the sorrower. Something like this took place in Judas, who after his repentance did not preserve his own heart, but received that more abundant sorrow supplied to him by the Devil, who sought to swallow him up, as it follows, And he went out, and hanged himself.

But had he desired and looked for place and time for repentance, he would perhaps have found Him who has said, I have no pleasure in the death of the wicked. Or, perhaps, he desired to die before his Master on His way to death, and to meet Him with a disembodied spirit, that by confession and deprecation he might obtain mercy; and did not see that it is not fitting that a servant of God should dismiss himself from life, but should wait God's sentence."

Two observations I wish to make are:

We must learn from Judas not to be consumed with our own sorrow for sins, and our own iniquity as this leads us inward, rather than to Christ who gives us salvation. Just as Judas should've turned to the apostles not the chief priests for his confession, or to Christ directly.

Secondly, that perhaps if Origen is right, if we make it to glory, we will be greeted by St. Judas. Wouldn't that be a wonderful image of how "where sin abounded grace abounded all the more"?