I think Dean can't stop thinking about Sam being in hell. He isn't taking the chances RoboSam's willing to take in order to get Sam out because he knows Sam wouldn't be okay with that, and he doesn't particularly give a shit what RoboSam thinks because RoboSam isn't Sam.
The problem I have with that theory is that it is, ironically, RoboSam who's doing the most to get his soul back. Dean's fighting Crowley tooth and nail which, yes, I understand he doesn't want to work with a demon, but Crowley's really the only person who knows how to put Sam's soul back in his body. I don't think Dean's quite grasped the concept that sometimes the ends justify the means. RoboSam may not be the Sam we've known for the last five years, but at least he's trying to get that Sam back.
Or Dean knows perfectly well that sometimes the ends justify the means and has concluded that this isn't one of those times. Or Dean's remembering that there's a reason Sam made him promise not to try to get Sam back. Or it's occurred to Dean that maybe Crowley's bluffing.
So Dean thinks it's better to leave Sam's soul rotting in Hell then? Or he has some massive Plan B worked out? Sam had Dean make him a promise, yes, but it's not like that worked out well. And even if Crowley is bluffing, it's a hell of a risk for Dean to take. Or, say Crowley is bluffing, the only possibilities then for Sam's soul are a) he's still down in the Cage, Crowley or no Crowley, or b) his soul is gone completely. At this point, Crowley's their only hope for getting Sam's soul back, and by alienating him, it's just making everything worse.
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...Which is weird.
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