Life is insane right now and I only have time to jot down personal stuff in the 5000 nanoseconds between errands, so this will grow, I'm sure.
Warning: this is how my un-structured brain works on 'no coffee' ...
He said it FELT like a week, like how you get to work and you are there for A YEAR and you get home and it's only been a day, but damn it was like a ... YEAR. Point being, I don't think this is a literal calculation he was making.
On the other hand, regarding souless! Sam, to fall asleep and fall back into the flames and suffer without your soul... Even one time would be enough to never want to sleep again. So, why not stay awake, since you can. *hugs souless!Sam who was only avoiding the hell in his dream that one time that made him kind of a dickbag*
On the other other hand, Sam will go (well okay, not gladly, but willingly) into the Pit for the next few however longs, repeatedly, because if he goes then no one else has to go. And that's the soulful Sam that we love. But it sounds an awful lot like another brother who did the same thing, who took the casting out and burned for centuries so that his brothers wouldn't have to, even though they were wrong about him ...even though their ideas weren't any better than his... It just sounds a lot like how Lucifer got to be the way he is. He's not half bad at being civil when he's here on earth, but he's twisted and dark on the inside from all that time in the Pit ... he has the kind of reasoning born of personal tragedy that wrecks havoc on everyone else... just when you think you are on the right side... but all you end up doing is saving the perps while innocent people get killed. When all you were trying to do is help the world... Show, I think I see what you did there.