Sword of Pain/Bereavement/Doubt in Mary's Heart?

John of Damascus, An Exposition of the Orthodox Faith, Book IV, Chapter 14

But this blessed woman, who was deemed worthy of gifts that are supernatural, suffered those pains, which she escaped at the birth, in the hour of the passion, enduring from motherly sympathy the rending of the bowels, and when she beheld Him, Whom she knew to be God by the manner of His generation, killed as a malefactor, her thoughts pierced her as a sword, and this is the meaning of this verse: Yea, a sword shall pierce through your own soul also Luke 2:35. But the joy of the resurrection transforms the pain, proclaiming Him, Who died in the flesh, to be God.

In this case, notice that John is suggesting that Mary escaped the pains associated with original sin at Jesus' birth, but nevertheless experienced them when he died on the cross.

Augustine, Exposition on Psalm 105 (Masoretic Psalm 104):

12. Next he does relate the story, mentioning what Joseph suffered in his low estate, and how he was raised on high. His feet they hurt in the stocks: the iron entered into his soul, until his word came Psalm 104:18. That Joseph was put in irons, we do not indeed read; but we ought no ways to doubt that it was so. For some things might be passed over in that history, which nevertheless would not escape the Holy Spirit, who speaks in these Psalms. We understand by the iron which entered into his soul, the tribulation of stern necessity; for he did not say body, but soul. There is a somewhat similar expression in the Gospel, where Simeon says unto Mary, A sword shall pierce through your own soul also. Luke 2:35 That is, the Passion of the Lord, which was a fall unto many, and in which the secrets of many hearts were revealed, since their sentiments respecting the Lord were extorted from them, without doubt made His own Mother exceeding sorrowful, heavily struck with human bereavement. 

While Augustine does not explicitly link it to sin and the fall, Augustine asserts that Mary was touched with human bereavement and consequent sorrow.

Basil, Letter 260, to Optimus the bishop, sections 6-9

6. About the words of Simeon to Mary, there is no obscurity or variety of interpretation. And Simeon blessed them, and said to Mary His mother, Behold, this Child is set for the fall and rising again of many in Israel; and for a sign which shall be spoken against; (yea, a sword shall pierce through your own soul also,) that the thoughts of many hearts may be revealed. Luke 2:34-35 Here I am astonished that, after passing by the previous words as requiring no explanation, you should enquire about the expression, Yea, a sword shall pierce through your own soul also. To me the question, how the same child can be for the fall and rising again, and what is the sign that shall be spoken against, does not seem less perplexing than the question how a sword shall pierce through Mary's heart.

7. My view is, that the Lord is for falling and rising again, not because some fall and others rise again, but because in us the worst falls and the better is set up. The advent of the Lord is destructive of our bodily affections and it rouses the proper qualities of the soul. As when Paul says, When I am weak, then I am strong, 2 Corinthians 12:10 the same man is weak and is strong, but he is weak in the flesh and strong in the spirit. Thus the Lord does not give to some occasions of falling and to others occasions of rising. Those who fall, fall from the station in which they once were, but it is plain that the faithless man never stands, but is always dragged along the ground with the serpent whom he follows. He has then nowhere to fall from, because he has already been cast down by his unbelief. Wherefore the first boon is, that he who stands in his sin should fall and die, and then should live in righteousness and rise, both of which graces our faith in Christ confers on us. Let the worse fall that the better may have opportunity to rise. If fornication fall not, chastity does not rise. Unless our unreason be crushed our reason will not come to perfection. In this sense he is for the fall and rising again of many.

8. For a sign that shall be spoken against. By a sign, we properly understand in Scripture a cross. Moses, it is said, set the serpent upon a pole. Numbers 21:8 That is upon a cross. Or else a sign is indicative of something strange and obscure seen by the simple but understood by the intelligent. There is no cessation of controversy about the Incarnation of the Lord; some asserting that he assumed a body, and others that his sojourn was bodiless; some that he had a passible body, and others that he fulfilled the bodily œconomy by a kind of appearance. Some say that his body was earthly, some that it was heavenly; some that He pre-existed before the ages; some that He took His beginning from Mary. It is on this account that He is a sign that shall be spoken against.

9. By a sword is meant the word which tries and judges our thoughts, which pierces even to the dividing asunder of soul and spirit and of the joints and marrow, and is a discerner of our thoughts. Now every soul in the hour of the Passion was subjected, as it were, to a kind of searching. According to the word of the Lord it is said, All you shall be offended because of me. Matthew 26:3 Simeon therefore prophesies about Mary herself, that when standing by the cross, and beholding what is being done, and hearing the voices, after the witness of Gabriel, after her secret knowledge of the divine conception, after the great exhibition of miracles, she shall feel about her soul a mighty tempest. The Lord was bound to taste of death for every man — to become a propitiation for the world and to justify all men by His own blood. Even you yourself, who hast been taught from on high the things concerning the Lord, shall be reached by some doubt. This is the sword. That the thoughts of many hearts may be revealed. He indicates that after the offense at the Cross of Christ a certain swift healing shall come from the Lord to the disciples and to Mary herself, confirming their heart in faith in Him. In the same way we saw Peter, after he had been offended, holding more firmly to his faith in Christ. What was human in him was proved unsound, that the power of the Lord might be shown.

In this passage, Basil does not just assert, but demonstrates that Mary was affected by sinful doubt.