Here is what the walkthrough says :
To find sleeping pills : search Doc Office at 16:00.
Go talk to Susan.
Now you need to blackmail Linda during “Naughty Doctor,” in her office at 21:00 when the door is
unlocked.
Wait for next dinner.
At 23:00 go into the corridor and enter Rachel’s room.
“Quick peek” and “Make Sure” for a little extra.
Go to sleep and wait for 10:00 then go talk to Susan.
And here is what follows :
The day after you use the sleeping pills, after dinner, you can hear noises coming from Rachel’s room.
Talk to Chloe and Emily about it, then Linda.
Search the bridge, it’s only possible when Susan is not here.
Now you need to wait for the repeatable to be available, it has a 4 day cooldown.
One the day Rachel miss the phone call, after dinner, go to the bridge and set the alarm then immediately
go into the corridor.
The next day, talk to Susan.
You can now enter Rachel’s room the next time.
How to unlock the contest:
You must have unlocked “Rachel's helping hand.