I cuddle my DD to sleep, for both naps and night time. She is 13.5 months old. We co-sleep, so this is why I do it. My mom watches her on Wednesdays, and at her house she does go to sleep by herself in a crib, so lately I have been trying to get her to fall asleep on her own at night, just because I have so much to do and I want to go to bed earlier. Every once in awhile it works if she can hear me roaming around upstairs, but for the most part she just cries. Sometimes when I think she is sleeping, and I try to get up from the bed, she immediately jumps up and grabs my hair so I can't go anywhere! I will admit that I do get a little frustrated at times, because, like you, it can her an hour to fall asleep. I've tried putting her to bed later and that makes no difference.
It probably is a habit, and will be very hard to break. When we are ready to move DD out of our bed (probably when we have another baby), we plan on getting her a youth bed and putting it right next to our bed, so the transition is a little easier for all of us.
Have you tried giving him a stuffed animal or a blanky to cuddle with? DD has never loved any of her blankies or stuffed toys, so I have been putting her to sleep with one, trying to encourage her to feel comforted by it. She wakes up about a million times between when she goes to bed and when I do because she knows I am not there yet, so I am hoping that, if she loved a blanky, then she could cuddle up to it and put herself back to sleep.