There might be a problem on day 2 when Lily comes home for her first night. Isn't she supposed to send an e-mail ?
The way the code is written will never allow Lily to send that email. So it's either a mistake or it is just useless to keep that code.
Game Version 0.44
File: story.rpy line #1219
Python:
if lily_email_first_night:
$ send_email(emails, Lily, 1, clock)
$ clock.AdvanceTime()
$ lily_email_first_night = True
jump MC_Bedroom
lily_email_first_night
Is set to False by default in: script.rpy line #306
Is never used anywhere else
Is set to True but after the test
The solution is to either remove the test or set lily_email_first_night to True before the test.