Once, and only once.
I played a teen mom runaway challenge: she started the game with literally no cash and a newborn baby. I spent so much time watching her eke out a living, struggle to keep herself and her baby alive, and eventually grow up to be a famous actress and a fantastic grandmother. Her little shack became a great mansion for her family, she had tons of adoring fans, and she found love with her make-up artist. Because of her, her child and his children have had better lives than she ever did.
But I wanted space in the house, and she wasn't dying of old age any time soon. So I had her stay outside during a heat wave until she died. She deserved better than that, but what can you do?