I thought it was interesting how Daniel K. Isaac's character (who by all means I'd consider the main character) is the Scarecrow rather than Dorothy. But the Scarecrow's goal in The Wizard of Oz was to get a brain, and in this show we see him "regressing" so to speak, getting closer to turning back into straw, unable to move his limbs, etc. And given that his home is in the midwest in a large field of wheat, I wonder if that's also a bit of what he wants to return to. Like he's now learned too much and wants to get back to that "ignorance is bliss" state, before he had to give up a portion of his life to care for his brother, before his boyfriend broke up with him, etc.
It's also interesting that people are getting taken by giant birds, which of course correlates mostly to scarecrows, and scarecrows are meant to be a sort of stand-in for when humans can't scare off birds but in this case the humans are the ones getting picked off, and the birds seem to be avoiding #1, despite coming close a few times, so maybe by regressing he is actually avoiding that fate?
And the other characters that sort of represent the Tin Man and the Cowardly Lion seem like they haven't quite figured out what they're missing yet (a heart and courage, respectively). And maybe being in the city means they've become inured to their flaws, or maybe that's the next journey for them to go on, similar to how Isaac becomes the narrator for Lavin at the end.
I don't remember where Callan said she's from, but I think it's the city? Which would be interesting considering that Dorothy's dream is to go home but she would already be home. And that could also be why she seems much more comfortable in herself, whereas all of Isaac's delivery seems a bit detached, like he's just reciting the things he's supposed to recite (I'm not pointing this out to be a flaw).
This is mostly just a stream of consciousness of the things I've been trying to think about when reflecting on the play, but would love to hear if other people had similar/different thoughts.