Hello, I believe the one for Roxy, you need go to the burning apartment and find little Roxy there, then you can bring Roxy to the daycare I honestly forgot since I played this game like 5 months ago and I can't download it again
You don't find Chloe in the Outskirts, you find a magical person in the Outskirts. Hint: she's small, green and opinionated. Keep using the "Explore" option and pay attention to the text hints when you find an "empty" location.
