I don't know your middle kid, but especially with the baby, it may just be the wrong time to institute any sort of cutting off. That may cause more trouble than it's worth. It's our special time along, and I'll read to you and rub your back so you can go to sleep. Then follow through. Number one, however, sounds ripe for the ministrations of a lot of Daddy.
Daddy gets to do the bath, read the story, and tuck into bed.
That removes one set of arms from around your neck. And as for nights out, if the sitter has to lie down to get them to sleep, so be it.