www.mytotclock.com will solve part of your problem. Ours has been sooo glitchy but even so, I love it and will buy another when it finally bites the dust entirely. Train him that when it's Blue, it's bedtime. He can come out in the morning when it's yellow.
Worst case scenario, childproof and strip his room of most items in the beginning and put his mattress directly on the floor. Not so far to fall, in the beginning we'd fine my daughter asleep and she would have rolled halfway across the room.
That's how we transitioned her the night she climbed out of her crib, but my son went straight to the toddler bed at 18 months when his hand-me-down crib was no good anymore.
Also, we really love our video monitor (we have the slim n' secure model by summer infant), and it's very useful to keep an eye on them!
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