To me, this was the most emotional episode of the rewatch so far. It is a Jack-centric episode. The flashback showing us his extreme inability to let go. On the island we have the fundamentals of the show. They could have picked any other episode to have Claire give birth or have Boone die, but it is interesting that they showed all of it happen in the same episode. I feel like the exemplifies the light cave: life, death and rebirth. I seriously haven't cried so much during an episode since The End.
The Life: I have said before, none of these flashbacks are random. Whether the characters are picking these memories to think about while they going through something on the island or what, they always mean something to they are going through on the island. In Jack's flashback, he is getting married to Sarah. Christian gives another one of his "awesome" parent speeches where he tells Jack he "can't let go." And that really gives us this base to the story of why Jack isn't giving up. But I don't think that is the entire reason this wedding situation was picked.
I think his marriage was picked because he wasn't really ever able to let go of Sarah. The Others even knew! Ben even mentioned that Juliet looked like his ex-wife. He re-bounded with Achara. It was more than just Christian's words here. It was the physical manifestation of those words into Sarah and into Boone.
The Death: Boone was the first major character that we see die. And it's so sad. I am under the impression that on island, there are two ways to die. The first one is completely letting go of what your came to the island with. And the second is never letting go of it (a la Nikki and Paolo.) I don't think Boone let go of Shannon. I think that is what made him a "sacrifice." I think that while he was coming to terms with his death he decided to let go and move on. Which is why we see him in the flash sideways, genuinely happy for Shannon and Sayid. When he said "Tell Shannon..." I like to think it was going to pertain his moving on.
Something I found really interesting while Boone was dying. He tells Jack that he can let go of him. I don't know if it is just coincidence or Boone was flashing sideways somehow here. Just another one of those things that we will never understand. Especially since we never got to see Boone wake up in the sideways.
The Rebirth: The most emotional part of the episode for me was Aaron's birth. What Kate says about Aaron was really beautiful. "You are not alone in this. We are all here for you. This baby is all of ours." And it made me think a little bit.. Maybe Aaron is special. Not in the "ZOMG Aaron is Jacob!!" way, but in the sense that they are all special to each other. If it wasn't for Aaron, Kate would have never agreed to go back to the island. The Ajira plan wouldn't have worked and who knows what would have happened. They are all pieces in a puzzle. Aaron is just as special and important as Jack is in my opinion. (And by the way - I totally forgot that Jin was just hanging out at Aaron's birth. Kind of creepy!)
Again, this episode wasn't too big on the island mystery. We got a lot of character here. (It is all about the characters!) But we did get a little nugget. I said last week that Boone's death serves purpose and I feel like one of those many purposes were fueling the fire to the feud between Jack and Locke. It was just more mouse trap.