Well, came across an interesting bug on the day where the MC feels sick. Maia is apparently in the Hotel Massage Room, but I cannot change time, and the MC appears to be asleep, but can be moved around.
*EDIT* Went to the Massage Room and massaged Maia, trying to see if that fixed things, but no dice. The MC is apparently stuck now. Attached is my save file with the issue if anyone wants to take a look at it.
*EDIT 2* Reloading the previous day and trying again seemed to fix it. Random chance seems to be working in my favor right now.