My oldest son was very sick beginning at age 9....he was in and out of the hospital for years and I would snuggle him in his hospital bed. My youngest is autistic and at age 9, was much like a 4 year old developmentally and he would lay in bed with his dad and I for hours watching TV and we'd all fall asleep sometimes...and he even watched TV with me when I wasn't feeling well and we'd both fall asleep and nap. Nothing weird about it. If my son was feeling insecurely attached, I'd get professional help and would allow him to sleep with me until he felt safe and secure (within reason) but I do realize I'm gauging this on some assumptions which might not be relevant in this case. Lefty asks great questions that I would need to know the answer to but ultimately it sounds like a professional could be valuable in this matter.