I think it is time to move Pumpkin to a big girl bed. I think that she wants to fall asleep laying down in her bed (and clearly she can do this, because she goes to sleep on her own at day care, on a little cot), but that she needs some help with the transition. The easiest way to give her that help would be for me to lay down next to her and let her play with my hair. After all, this is what works in the middle of the night, when we bring her into bed with us.
I've been trying to do this with her in her crib, but it is uncomfortable for me (I end up with my face smooshed up against the bars), and doesn't really work for Pumpkin.
Also, she seems to be getting tired of her sleep sack. It is only a matter of time before she can get herself out of it- she can already unzip the little sleep sack my Mom made for her baby doll. It seems like moving her to a big girl bed would be a good time to swap the sleep sack for a regular blanket.
I can envision a whole new bedtime routine, in which she gets in her bed for her bedtime stories, and then one of us lays down next to her while she goes to sleep. And then, if the sleep gods finally decide to smile on us just a little bit, we somehow slowly transition her from needing one of us there to fall asleep.
Hubby doesn't see things this way at all. He sees her getting up in the middle of the night and wandering around the house once she is freed from her crib. He thinks we should leave her in her crib as long as possible.
I know I'll win this one eventually (who ever heard of a first grader who sleeps in a crib?) but I wonder if I'll win it before the current bedtime routine ("Mommy stand up." "Mommy sit in chair." Mommy rocks Pumpkin to sleep for 20+ minutes in the rocking chair.) makes me crazy.