I think that means you win the degrees of separation thing.
I kinda thought that whole musical storyline, specifically Lorelei being the only one critical of it, underlined how she was stagnating rather than being content with how things were. The Wild business was much more watch from the hall for me. Ugh. Fun bit for Peter Krause, though.
To be fair to Rory, I don't think she thought of the Chilton possibility as settling until the headmaster said he was trying to help her. It was just a possibility she hadn't considered when he first mentioned it. If he'd followed that up with "seeing how good you were with the students just now, we could really use someone like you here" would have given her an entirely different attitude about it.
Loved Emily's journey, and Lorelei's made sense for her, Rory's...in a theoretical way I like that she's hitting that "but what if I can't make things go the way I want them to" point that is so hard for successful good-student types when they finally run into it, but her romantic choices are baffling to me, to channel Tim Gunn. I did appreciate her easiness with Dean (so weird to call have JPad be "Dean") at the store, that was nice to see. I'm concerned that they are setting things up for some kind of parallel - having Rory is what gave Lorelei direction and discipline and whatnot and now Rory becoming a single mother will be her own true path to happiness. That would be...disappointing. I did like how the last scene colored the earlier scene with her father, though. The questions make a lot more sense.
Seeing everyone again is just so fun. A little too much Kirk in the first hour, but just about right in the end.