Chuck is currently leading Supernatural again.

Do the airdates roughly reflect the dates in the eps? Is that an okay assumption?

Do you mean the dates in the show? If so, no. They skipped ahead a year when we skipped ahead the summer.

Would Swan Song still be in line with May, though? Does it even matter?

Approximately. I think the last time they concretely matched dates was MBV. However, apparently there was a flash of calendar in a fall episode that had a fall 2010 date on it, so that was wrong. Also, when they dimension hopped, they hopped into S6, which may or may not be meaningful.

Matter?

Everything matters.

Right now, why do Dean and Sam hunt? Because they're the only people who can do what they do? Do they not trust anyone else to hand over the Mother/Purgatory issue to? Do you think they're looking for a break so they can quit, or they would like to keep going under non-soulcrushing apocalyptic conditions?

I think the Mother/Purgatory seems dangerous/bad enough that they probably think they need to be the ones to handle it, and there might be an element of guilt or responsibility there, as well, if it turns out to have anything to do with the failed apocalypse or Lucifer.

I also think Dean really doesn't know how to do anything else. Sam's wishes were enough to drive him to Lisa and Ben, but even while he was there he kept looking for ways to spring Sam the whole time. And even though he came to love them both, I think he's too convinced of the danger to them, both from what he does and who he is, to stay with him.

Sam is, I'm pretty sure, trying to atone for pretty much everything. He's going to want to hunt every monster he can and save every innocent person he can for a long, long time to make up for Lucifer and his Robo year.

There's also the possibility that Dean has drawn a connection between the Mother of All/all monsters go to Purgatory situation and Death's request for him to look into what's happening to people's souls.

Do you think either of them like it? I guess I feel so good about their brotherly bond right now, I want to feel a bit better about their lives. And I'm reading people talk about Dean's hatred of hunting, and it's sadface.

(I'm cheating and rewatching last week, and RUFUS!!! Also, SAM! I'm watching the scene where they find Dean after he shoots Gwen, and Sam has this "Who do I shoot first?" look on his face that's positively adorable and I want to smish him to pieces)

In conclusion: RUFUS!!!!

Oh, I think they're both glad to have each other back in a way they haven't for a long time. As far as we know, neither of them is destined for some great doom at the moment, and neither of them are being manipulated by demons or angels. (Except for Cas, and I'm willing to accept that they're both okay with that, after the fact -- they give Cas a lot of leeway for good reason.)

And I don't think Dean hates hunting at all. I think he gets *weary* of all the evil there is to hunt, and especially of feeling like a pawn, but in the moment? I think he loves the chase and the kill and the satisfaction of doing something few other people can do.

He's a thrill junkie to some extent, so there's always going to be that adrenaline rush for him, I think.

(God, I have such a fierce love for this episode. The door just slammed down between Sam and the rest, and Dean! Sam! Dean! Watch yourself! And now Sam will kill his grandfather because it's the right thing to do and I can't believe they had a hero kill his family not in explicit self defense and I love this show)

I think Dean hates himself and any hate it appears he has for hunting is more his low self esteem issues than actual hate of the trade. I'm sure he doesn't hate what his brother and father did, although he probably hates that he had to do it. I like to think he can at least take pride in a job well done, and lives saved.

It doesn't strike me that they feel solely responsible for dealing with Mother. Like it's not even a thought as to whether it's their business or not. It's habit, it's a lifestyle, they stumbled onto something, and their dealing with it. Maybe there are other hunters out there who are also dealing with it, but that's not their problem. Maybe they're not happy with it, the Big Hunt, the lives they lead, but they lack the capacity to think they could walk away from it. And Dean tried that, and first tried to have both worlds, and then deliberately walked away from it after his big epiphany that YES THIS IS MY FAMILY.

And Sam wants redemption. And Dean won't let him look at what he's actually responsible for. So if there's redemption to be found in righting other wrongs, then Dean's on board with that /spec

But until they come back to Dean's self-evaluation from YCHtT where he considered himself a killer (he's stuffed that shit down, y'see), he's as happy as he's gonna get for now. And Dean being happy having Sam is Dean being happy in the life of a hunter or any kind of life.

Was Dean happy in season 1?

He was a total faker there. More innocent, maybe, but even then I wouldn't call him happy, believing in non-attachments. Even without the trauma of him losing his dad and then Sam and then going to Hell, Dean's season 1 delusion of carefree solitariness would have eventually crashed down on him.