We don't do "co-sleeping" every night, but we are really fine with having our daughter sleep with us when she feels she wants to. She always starts the night in her bed (well except for this weekend - you can read about that on my blog) but often ends up in our bed before the night is over. She is 3yrs, 3 months. I remember crawling into my parents bed in the wee hours of the morning - maybe it was a bad dream or whatever. It wasn't specifically co-sleeping, but it was the reassurance that I could go to them if I felt that was where I should be.
What you might want to try is to lie down next to him in his bed until he falls asleep. That way, its a bit of both worlds.
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