DS slept with us until about 10 months when it stopped working for everyone. Then I moved him gently to a crib. He really liked the crib, so I was a little worried about moving him. He's just now moved to a big boy bed just shy of 2.5 years old. No real reason other than that I wanted to transition him before the baby comes so he doesn't think the baby is taking his bed in the same way.
I took him to the furniture store to pick out the bed, we ordered it and talked about it for the 2 weeks until it came. He ws pretty excited. I made him a special quilt for his bed. The day the furniture truck came, I let him watch the whole process. He doesn't speak very well, but he was still telling the assemblers "big boy" and pointing it at. That night, he slept in it with no problems. He's only gotten up a couple of times, and I just remind him that it's bedtime and tuck him back in. Two nights ago, he was sick, so he did sleep with us.
I put up a gate at his door, so when he gets up, he just calls for me. I would worry about him getting hurt in the house otherwise.