This art? FUCK YES. Landlady/roommate? Fucking patreon. Although at this point I am already instinctively seeing mom/sister whenever I see those two used in a game.
If suggestions are being thrown around? I love a good twisted common sense scene. Lets suppose the rent is due but the main character has set it up so the landlady believes that rent is paid in semen, which she diligently collects from you (comedy dialogue maybe "hey, is this everything? You better not be holding out on me."). Possibly she collects it all in a cup and drinks it? If the game is having slightly complicated stuff then have a separate set up where the roommate believes semen is an excellent health drink and is sucking you for it. When both of the above scenes have occurred an event can happen where roommate drinks the "rent" and then, under the supervision of landlady, she has to help you pay the rent again.