No, he didn't know while in hell that Sam was using his powers. But when he got out of hell and found out, I'm thinking that part of what pissed him off, besides the fact that Sam was using his powers at all, was the fact that Dean's being in hell, having sacrificed all of that, was of no use. There he was in hell, suffering, holding close to his heart that all of the suffering would save Sam. Come to find out it didn't.
Which doesn't answer the question as to why he broke after 30 years. : D
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Which doesn't answer the question as to why he broke after 30 years. : D