It's easier if you give a pic, because I don't know if you count row first or column first
Anyway, row first: 4th pic you need to send the drone to roommate's window in the morning after she go back from the shower and 12th pic, after you get the task upgrade the drone (buy the upgrade from the store) then send it to barbara's pool at night (maybe you need to send it multiple times to get the scene).
Column first counting: 4th pic, you need to give her the new yoga dress, then open the door in the morning right after you get up. Don't forget that you have to oil the door first! And then just watch the scene. 12th pic, well, you need to use the sleeping pill on her coffee in the evening in the kitchen, then at night go to her room and "play with her".
For the first time, not, because then the "fuck scene" appear, so just massage her and click on the spot. She will turn and you can massage her breasts and get the pic. After she will turn back and you can use the oil.