You have to:Hmm. I tried that path and you don't get to listen in. Only get 1 choice and that's to go to the gym.
Approach landlady calmly
go straight to living room for picture
after your nap:
continue down hall, (do not look in bathroom) this alerts landlady so she closes bedroom door
Go left on stairs
check first room, (door should be open) if you go to upper hallway door will be closed (room 4)