I'm on the same page with Mom of 4. I like starting with the youngest because their transitioning is usually easier and you can teach them/have them adapt to your setting a bit easier and more naturally. I have one 3 year old who had crazy separation anxiety so it put me off on taking older ones, though I do see the benefit of them being already independent and able to do so much more in terms of play and activity. So with #1 it would really depend on her personality- if she was outgoing/independent/comfortable on her own, how she is in leaving mom, whether she had been taken care of by someone else previously, etc. 1 or 2 would be my option for sure. But #2 would be my choice in terms of securing my income for longer. And having a family you love working with who appreciates you and thinks the same in return is worth everything to me.