Hmm, good question. I think in Sam and Dean's case, speaking for myself, it matters that when they do not-so-good things to save each other, it's not a direct act of evil. Dean's first deal hurt himself only -- directly. The impact on Sam and the path Sam spiraled off as a result was indirect and in part became part of Sam's choices. Sam released Lucifer... but Lucifer is responsible for his own kills, not Sam. Not directly. When Cas released the Leviathans.. again there is a pattern of the damage coming from something bad being released, but the evil being done isn't directly done by Sam and Dean. Now with the Darkness and all... They know there will be consequences, dire consequences, but it seems a step removed from directly strangling or shooting or killing, etc in the name of saving the other. We have seen them torture/kill something evil, but again... never to my memory someone who was purely innocent. Not directly. They are the collateral. It is a small distinction that doesn't absolve them of the responsibility for the consequences of their choices, but I think there is a difference that makes them far more forgivable, at least for me. And at the very least, they take responsibility for what they did wrong and try to fix it. That is key for me.
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