Dear Undo.
I like the Spiritual Symbology within your dreams -- The Vine of Christ and the Light. and your Dream points to a Truth that Catholics know of more from the experiences of their Saints than because of any positive Doctrine or point of Faith, and that is that Penance and Suffering done for Atonement are commodities that can be transferred from Soul to Soul. Often Saints have deliberately incurred great sufferings and served stringent penances in order to ameliorate the conditions for the poor souls in Purgatory, even to the point of freeing them for deliverence into Heaven.
Oh, which brings to mind the distinction between hell and Purgatory. Your boat from hell, in your dream, from which one of your old friends returned.... Hmmmmm. No one returns from Hell (though there are some ruminations that Our Lady may be contemplating a means of purifying and lifting up even these stink-ridden predators and human beasts), but Purgatory, for souls with some innate goodness in their hearts though they be stained with some horribly bad habits, Souls only need to stay in Purgatory until they are Purified.
Purgatory was in interesting development. It was not a natural place and did not already exist but was specially created by God for a purpose that had not been anticipated. Originally only the Highest and Purest Souls were to be admitted into the Kingdom of God -- within the Holy City, that is, to be in the Very Presence of Holy God Almighty. Those of innate predatory evil and irredeemable beastliness would be sent to the wastelands of hell, to be forever separated from souls of those who appreciate Community and moral goodness. But souls less than perfect would be allowed to live in the great middleground -- protected from the demons of Hell, but because of their impurities and imperfections, not allowed into the Holy City of God.
To everyone's surprise, some of these Middle Zone Souls would be so disconsolate at being segragated from the City of God that they would go to any extreme to enter into whatever Light of God they could find, from any crack or reflection from the Holy City. Now, you need to understand, that the Light of God BURNS like a Fire when it is absorbed by any Imperfection. If one's Soul is Pure and Translucent, like the Clearest Glass or Crystal, then the Light of God can pierce through without transferring any HEAT. But any opacity, spot or mist will burst into Flame. Very painful! But the Souls were eagerly seeking out just such opportunities. Frankly, it took God Himself by surprise. Anyway, God decided to systematize the process.
Oh, and regarding the transferrability of Penances, Catholics consider it quite important to pray that Light be sent to the Poor Souls in Purgatory so that they may be sooner than later purified and be made worthy to enter into the City of God. It was one of Satan's greatest victories, in establishing the Protestant Sects, that such a great portion of nominal Christians are taught on their mothers breasts to renounce any belief in Purgatory and pointedly instructed to never pray for their dead.
Anyway, I do not think you will be going to hell, but rather that you are spending some time in Purgatory, taking upon yourself the impurities of this Lady you are standing in for. You have quite the instincts of a Saint. and you should remember that Souls whom you free from Purgatory through your Penances, Prayers, and Atonements will be eternally grateful to you. You could do worse for yourself.
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