There was a black hunter that wanted Dean dead, I can't remember his name. (thats rhetorical btw). Do you think that when he went to hell; if he did, he escaped when the devil's gate was opened?
Do you reckon that Dean tortured his Dad in hell?
Do you have to be a demon to escape hell, if a devils gate is opened?
When sam was killed is the reason why he couldn't remember anything because a (good) reaper hadn't yet collected his soul?
Is a demon boss, for example, Alistair or Lilith stronger than an angel?