We cosleep for part of the night - DS starts off in his crib and ends up in bed with us at some point inevitably. We got his crib when he started rolling around like a maniac at around 6 months, so the crib transition started then and has been going steadily for almost 4 months now. For some reason he will sleep in his crib (in our room) before we go to bed and are not in the room. Once we get into bed, he somehow senses our presence or something and will wake up as soon as we get into bed so we bring him in with us. Maybe it's just his/our habit. Anyway, some nights we can put him back down in his crib, others he won't go back down in there only in bed with us.
For naps I found it was way harder to get him to go down in his crib at first. These days it's getting easier and easier. Sometimes I try and if he wakes up then I'll put him down in the bed and give up. I found lately that he goes down really easy in the crib when he has fallen asleep in the car and I just put him in the crib when we get into the house.
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Anyway, my point is I think it is just taking time and effort- the more I try to put him down in there, the more he does go down for naps in his crib. Maybe he is just getting used to it, maybe I am getting better at putting him down in there. I dunno. My goal is to have him napping and sleeping in his crib most of the time by the time he is a year old- but I'm not rushing him. If he is ready to do it he will. When he wants/needs to sleep or nap with me, he can.
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I have books and a laptop in the bedroom for when he is sleeping on the bed. Sometimes I'll fold laundry or do something like that while he sleeps. Yeah...it can be boring, but it's still a nice break.