The doctor's office should appear as a date location & if you go there with a girl, the focus will be on her. Once you have a prescription for her, you should be able to buy medication for her at the pharmacy. Let me know if that's not appearing for you.
Good idea about asking girls to give up their jobs, making them more available at home.
I hadn't thought about making the girl's home more like the player's. That's something I may add in a future update!