Well, you may have figured out (and it helps that I think I mentioned it) but we made the switch from crib to toddler bed this weekend with Peanut. While he hadn't attempted to climb out or anything he was: waking at night, waking at 6am and hollering only to fall back asleep in my bed, sticking his legs through the slats and getting them caught and his favorite bedtime game was throwing everything (pillow, blanket, stuffed dog, binkie) out of the crib. Then naturally, he would cry and want it all back.
So his actions combined with the fact that I had finished Sweetcheeks' bedding and was anxious to see it on a crib, led to making the switch on Friday. We chose naptime vs bedtime because that worked really well with Pooks. I think it's less intimidating and easier to adapt to a change at naptime.
At first it was a bit rough. I would say ''Okay, time to get in your bed Peanut" and he would climb up in Bubba's bed. Umm, no. Then I repeated "No, your bed." and he pointed to the disassembled crib. Umm...not quite. So after laying him down in the bed and him promptly getting up, and me laying him down and him promptly getting up, I realized this wasn't going to be as easy as we had hoped. It ended up with me sitting on the edge of his bed and each time he started to get up, I'd lay him back down. After about 5 minutes he didn't sit up. He pretty much ignored me until he fell asleep all of 3 minutes later.
Bedtime was the same thing. I sat on the edge of the bed for about 10 minutes until he settled in and his eyes got heavy, then left. Each naptime/bedtime since then the amount of time I had to sit next to him has decreased. At naptime today (day 4) I didn't sit by him at all and he never once got up! Overall it was still a pretty smooth transition despite a couple of kinks.