(though as has been pointed out on my flist this morning, is he really the first righteous man in all of time to be broken in hell?)

So here's an interesting thing.

Righteous souls don't go to Hell.

So, what was Dean doing there? He sold his soul; that would make him unrighteous.

Except, apparently not, because he broke the first seal.

So, selling his soul to save his brother wasn't an unrighteous act? Or something?