Thanks Quid. I like that idea of Dostoevsky's too. All the same, I think distinctions, such as those between mortal and venial sin, are still possible and useful. Your idea reminds me of something like the Sorites paradox, where a certain vagueness in definition or knowledge is said to prevent a distinction altogether. Yet we can say with confidence that--ceteris paribus--to murder someone is more grievous than to steal half a day's wage from them.
My worry is that once Dostoevsky's principle is applied in anything other than a mystical context it has a tendency to become destructive of human responsibility in that no differentiation of sin or sinners is allowed. Further, the principle--and especially your interpretation--is consequence-based. It may sound odd, but I tend to place that consequential analysis more in the realm of natural evil than moral evil, particularly when we are talking about unintended, unforeseen, and especially unforeseeable consequences. For example, a just judge wouldn't charge the man who stole the candy bar with homicide, to take your example.
If we can't differentiate sin and we can't give a special priority to the evil of the proximate act itself (as opposed to its unintended consequences) then I'm not sure the moral understanding of life will survive. The key with respect to culpability is the act itself and the intended consequences, not unintended or unforeseen consequences. Morality really needs to focus on that aspect of malice or selfishness, and the danger of Dostoevsky's principle is that it draws us away from that.
Finally, I think there is a practical point to be made. Much of what you say is undeniable. We don't know the full consequences of our acts, we don't know what we are contributing to, we don't know how our sin will interact with other realities, and yet we still have to act day to day on the best knowledge we have. It's possible that our theft of a candy bar will lead to suicides, and it is also possible that a vengeful murder of a man will save millions of lives (if, for example, that man would have grown to be Hitler). It is also quite possible that we will make mistakes of self-judgment and will be judged differently by God, either above or below our own expectations. Even despite these possibilities I am comfortable presuming that murder is a mortal sin and stealing a candy bar is a venial sin.
One of the objections I noted in the OP was that it is sometimes hard to know which is which without some external legislator. One of the "pros" I gave was much the opposite: with concrete categories it is harder to deceive oneself and call a mountain a molehill. In Catholic teaching gravity is determined primarily by the object/species of the act, rather than the intention, even though the intention is important and can aggravate a sin considerably. That is to say, the sin is primarily judged on the basis of the action that is being carried out. Now if I am murdering people and I see a Publican murdering people, and I still hold that I am far and away above the Publican, then I think that problem must be traced to human nature rather than the doctrine of mortal sin.
The other point is that it isn't clear why the doctrine entails a "decision to label some sin less than another" rather than a decision to label some sin more than another. A common Lutheran objection would be just the opposite, that the doctrine of mortal sin leads people to believe they are in danger of Hell when in fact they are not. I take it that the same point could be applied to Dostoevsky's idea. Sinful acts could lead to good outcomes, such as that "felix culpa."
Perhaps a good way to approach the issue is to ask, "Is someone who believes in mortal sin and venial sin better off than either someone who believes only in mortal sin or else someone who believes only in venial sin?"
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