Some very wise words, Fr. Gregory. Here, at least to me, is the voice of the Lord whom I have encountered.
I wish I had had your words about eight years ago. My closest friend, who became a Catholic, found his journey almost derailed by akriveia. His belief, which despite all his efforts I have never been able to share, that the Pope is indeed the rock upon which the Church is founded, drew him to the RCC a few years before my own journey brought me to the BOC. His local Catholic Church welcomed him and everything was lined up for his reception. Then, in a casual conversation with his priest the latter discovered that his 'convert' had been married, divorced and remarried; everything, to my friend's distress, was called off.
I spent hours, indeed in sum many days, trying to do what I could to help. He was in a very bad place. He showed me the letter he wrote to the local diocese and his priest. I will not break his confidence, but he is quite happy to let me say that he wrote to say that since he believed that there was no salvation outside the Church, and since his past sin was now keeping him from the Church, he felt his soul was in danger; it was as though he had committed a sin which could have no forgiveness. How I wish I had had the post which you have put here, back then.
In the end it was all resolved. He had married thirty years ago and divorced twenty years ago. With the help of the local diocesan official who dealt with these things, he was, as they put it, able to 'find a loophole' and to annul that first marriage. This meant further upset to his first wife, but she agreed so that he could do that which he felt he had to do. The whole thing left a sour taste for some of his friends.
How much better is the approach you outline. Of course we are not God and cannot judge as He does, but we know He is love, and we have, as you point out, enough examples of His impatience with those who carry around big baskets full of rocks (I love the way you put that
What made it all the sourer was the fact that a notoriously unfaithful friend of his was declared to be 'Catholic in good standing' when he also approached the RC Church - because his long-suffering wife had never actually brought herself to leave him.
All of this left me looking on, and to this day he cannot understand why, despite his best efforts, I cannot follow him. It is not just that I don't share his conclusion about the Pope (although I am happy with the concept of a primacy of honour) it is the mindset which the actions I have described seemed to betoken. That seemed legalism taken to extremes (as it usually is).
Of course, it takes time to get to understand the circumstances of the individuals, and to come to an inner understanding takes prayer and discernment, but if the priest is to bind and loose as the Lord does, He must surely strive to acquire these things? The mindset you describe seems to me the path down which the truly penitent can travel. I shall never forget my friend's distress for the year and a half it took to resolve his 'irregular' situation; nor the charity of his ex-wife in accepting what she felt was an entirely unfair verdict on her only marriage.
In this is love, not that we loved God, but that He loved us and sent His Son to be the propitiation for our sins. (1 John 4:10)