For quite a while, we were "Family Bed" co-sleeping. Now however, we're branching off to the "side car arrangement" or different beds in the same room. So far George is doing quite well with it. The bed arrangement now is with George's baby mattress right next to our bed, on my side.
On the first night, we put George straight from his car seat, sound asleep, into his bed with his new favorite stuffed animal, "Bunny". In the middle of the night he stirred, and was calmed by a simple hand resting on his back, and looking up and seeing me he closed his eyes again. A few minutes later though, he stood up with his arms held out, and was asking to come to bed with us, and I obliged. You don't have to rush these things, and just need to have patience I figure. That way it's less traumatizing for him and me alike.
On the second night, last night, I nursed him to sleep on his mattress, gave him praises on how responsible he was and kept giving him Bunny when he was wanting to get up on the big bed. Finally he settled down on his bed, and finally fell asleep. It took a lot of couching, but there wasn't drama and it was all good. In the middle of the night he was able to be nursed asleep, but the second time he ended up needing to come to bed with us again. Its slow, but I'm very thankful on the great start!!!
Trying to wean him is tough too, but I think its important so my body isn't healing itself and feeding both a newborn and a toddler at the same time! I'm trying to get him to turn to chamomile tea instead, and so far George has almost cut back to where he was, before my milk kicked into double gear in the middle of pregnancy (he was already weaning himself till that happened and then everything went in reverse!). He's still getting nap and bed time milk, but now that he's picked up his milk time has curfew times, he comes up to me and makes a cute face and says "milk-a-boo-boo!" I'm sorry, I can't say no to that! I'm offering chamomile tea with milk and giving it to him whenever he accepts though, and am happy milk production has toned down! He's a big boy, and I'm sure things will work out in its own time accordingly. :)