I think the Thanksgiving scene from heaven, as well as Sam with dog, shows him wanting normal. And I think even in S1 when he wanted to go back to school after they killed the YES, that was part of wanting normal, too.

Even in After School Special, the paper he wrote seemed as much about railing what was abnormal about his life as it was about not being constantly in danger.

I really need to rewatch the Heaven episode to recalibrate the emotional content of those scenes in regards to normal vs. safe. Because my takeaway from the Thanksgiving scene was that he was feeling very much like an alien in an unfamiliar world. He may have wanted to learn about it, may have been curious about what it would be like to experience a "real family Thanksgiving," but I don't remember him looking as though he felt at home. But I could be totally wrong. And I remember him thinking of the time with the dog as an adventure and a brief span of time with the pet he always wanted. But I don't know that Sam would regard squatting in those conditions as normal.

Now going back to Stanford, that I would view as a return to "Normal" for him. He had built a life for himself there, and was envisioning a future. (Is 'envisioning' a word?)

Envisioning is a perfectly cromulent word.

I can see 'safe' and 'normal' as both being other ways to describe stability. Staying in one place for more than a few weeks at a time. Being able to have ongoing relationships that didn't have very high odds of being severed violently. Etc.

Dean, I see as wanting normal at some level but suppressing that desire for any number of reasons. I remember his delight at mowing the lawn in WIAWSNB, of being a PA in Hollywood Babylon, and then dreaming about having a life with Lisa. PTSD issues aside, he seemed to adapt to his new life with Lisa reasonably well. If he had those suppressed/repressed desires, he might well project them on Sam to some degree.

I'm not sure they had it all planned out as well as Kripke claims they did.

I think there was a fair amount of handwavium involved in their planning. Also, maybe the planning was more of a general road map from A to B to C to D, with details being made up as they went along. I can also imagine a situation where Cool Idea 1 ended up getting trumped by Cool Idea 2--but with no way to go back and tweak details in episodes that had already been filmed and aired.

PTSD issues aside, he seemed to adapt to his new life with Lisa reasonably well

I'm not sure what to blame all that drinking on. PTSD, Sam, misfit, whatever. But I think he adapted to caring for Lisa and Ben better than he adapted to normal life. Part of this is my own personal fanon, but still. It's not like I'd expect an experienced hunter not to take precautions, but his night patrolling and his gun under the bed in a house with a kid in it isn't quite fitting in.

Hard to tell with what we were given, though.

On whose orders was Anna acting? Can someone go to a convention and ask that question?

When she was sent to kill Sam?

Yup. I remember assuming it wasn't Michael, because he ended up killing her, but I'm fuzzy on if I ever decided on anything.

Also, dead or not dead? I just read someone saying she wasn't. Lack of wing imprint?

I'd have to watch that episode again.

I'd say dead. Supposedly she wasn't in a host, but instead manifesting a facsimile body (like Castiel), so the special effect might be different. Michael gave no indication that he was being merciful.

Well, she couldn't be working for Zacchariah, since he wanted Sam alive and well so Lucy and Micky could face off. It seems like it would be some unseen faction of angels who just wanted Lucifer DED, and thought they were actually doing the world a favour? You know, one human dead to save billions?