Actually, after further testing, this does work as intended. Granted it is a bit convoluted.
- Meet with Annabell in the church during Day 1 and talk to her 3 times.
- Meet with her on Day 2 and help her with the care packages. Pick any option apart from 'stand up for yourself'
- Meet her on Day 3
- Have her father help with the shower
- Meanwhile, check in with Chance to get the ID. After meeting with Chance, make sure to go back to Annabell so you can get the photo
- Talk to Annabell on Day 5. She'll want to meet during the End of the Day.
- Make sure to talk to Chance before the end of Day 6 to get the ID.
- Talk to Annabell on Day 6.
- She will come around on the End of Day 6. If you don't have the the ID, she will stay with you. Otherwise, if you have the ID or are letting the two band members stay with you, you can take her to the show.