So, Nolan has taken to his toddler bed in his own room better than I could have hoped. He happily stays in bed at night, and even stays there most of the time when I put him down for his nap. We've only had one bad night where he had to sleep in the Pack N Play for part of the night.
Our current problem is that he's getting up really early in mornings. We think it's because there's so much more light in his room than in our room.
So we're shopping for a way to make his room much darker. I bought the blackout curtains, and honestly they don't make the room any darker than his old curtains did, and they are stiff and won't pull to the sides to open them to let light in during the day. We bought a roller blackout shade, but the stupid thing is worthless and won't stay rolled up at all.
I'm an avid Dave Ramsey fan, and have been listening to his podcasts almost exclusively in the car for a few months. One of his main advertisers is Blinds.com. I decided to price them on cordless blackout cellular shades, and they truly are less money than anywhere else I have found. So we've ordered some samples to choose a nice neutral color, and then we'll suck it up and spend the money on his window treatments - cause our sleep is worth it! :)