Just over a week ago we finally plucked up the courage and took the leap of faith to finally put Cole in both his new room and his new toddler bed. The baby when she arrives will make Cole's old nursery her home along with his crib.
Things have gone surprisingly well.
We were a little scared that a new room and a new bed would be a lot of adjustment all at once. I wasn't too concerned about the evenings. Knowing that it would be dark comforted me in knowing that there wouldn't be too much playing instead of sleeping. Nap time however made me really apprehensive. Cole was already protesting his naps and skipping the occasional one. With no bars to keep him in I was sure his afternoon naps would be something of the past - bad news for a mother 7 months pregnant and desperately in need of her own afternoon reprieves.
Cole has amazed us.

The first 4 or 5 nights Cole cried when we left the room. We are pretty sure he was simply confused as to what was going on and why his almost 2 year routine was being disrupted. After about 20 minutes to an half-an-hour of crying I would go back into his room and sit with him on my lap. He would calm down and then babble away. I would then place him back in his bed and talk to him some more, letting him jabber away about whatever was concerning him. After a while I would tell him it was time to go to sleep and lay him down and then leave the room saying all the good nights and I love yous I normally do. We would still occasionally hear him trying to open the door (he hasn't figured out door knobs as of yet - thank goodness!)) but he would eventually climb back into bed and has fallen asleep there every night.
Nap time was a slightly different story. On 2 occasions Cole simply fell asleep in front of the door either playing or waiting for mommy to come and get him. I would regularly hear the twang of the doorstop, however, no melt downs or loud protests.
So as of right now Cole is falling asleep in his bed every night wonderfully. In fact even better than in his crib when he used to stay awake for almost an hour playing and babbling to himself. The past four nights we haven't even heard a peep. As for nap times, the majority of the time I hear Cole climb out of bed and play, but he has eventually falls asleep after climbing back into bed. I quite often find the books I leave on a stool next to his bedside snuggled up with him.
Cole seems to love his new big boy room and bed, and there has been no mourning for the old crib and nursery, where the door remains closed most of the time while mommy does some re-organizing. Both rooms needs some additional decorative touches that Grandma will help me with next week when she comes to visit.