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(+1)

Anyone know how to do the libido supplement route to wake up the landlord???

(+1)

Buy Libido supplements > Check the cabinet in the bathroom when everyone is in the house and not sleeping. This activates Libido supplements routes.
For the ones where the $landlord does stuff, you also need to have him feminised by buying the Estrogen pills and spiking his Dinner.

After the steps above are completed, go at Night in their bedroom (Lockpicks needed from the Market), the option will be there.