No more crib

We are trying to combat the bad habit of letting William wail his way into our bed at night. Nang thought a good cry-it-out approach would work again (he got William to sleep through the night at 13 months with his version of the technique), but I warned him to keep a close eye on the monitor because the little guy was close to figuring out how to hop out of his crib. One big thud later (no tears, so we figure he landed somewhat softly), William's sleep setup looks something like a college apartment. We still have no idea what to do about getting him to sleep at a decent hour (wide awake picture below was snapped at 10 pm) and keeping him on the mattress in his own room through the night...little steps.