Maybe he'll uncover a small door and find an Other Mother.

But it was blue wallpaper, not the yellow wallpaper.

We saw the same episode. 
I was moved also by seeing the cooks at the diner collapse onto the counter stools when the MLK assassination was broadcast.  Also Ginsberg's Pop covering his face in mourning was evocative of Jewish funeral customs.  That was touching and genuine.
Very happy with your recap here, R.A.Ticker.

Yes, he feels no discomfort with the Drapers and the Rosens out to dinner because Dr Rosen and Mrs Draper are good company.  Uh. Huh.  He left his empathy in his other coat.

"But instead of just coming out and saying to her “You’re also safe,” the
judges made it seem like she had to earn her place there by completing
the oh-so-monumental task of staying in New York and thinking about
where she went wrong? She just got the Project Runway equivalent of a
time out."

Re: 1 - "Death! Death!! DEATH!!!"  I came away from the show literally shouting, "Death!" with the image of The Lord of the Rings: The Return of the King film with the Riders of Rohan charging onto the fields at Minas Tirith in my head.

You are right.  We have an old shoeshine box in our house with which I tried to inculcate my son into the art, as my father did me.  (Still waiting for him to get a job where he needs good leather shoes.)

Yes, 3hares, I also can't imagine Weiner doing a 'where are they now'? postscript.  It's been done. (Six Feet Under)

I took the shoeshine reference back to when Roger sang "My Kentucky Home" in blackface at his country club party.  Has he evolved since then?  Possibly.

It seems to me that the most obvious (and significant) of these doors is the seedy Village door: