We cosleep, so I cannot just leave him by himself.
I know a lot of you have children who don't sleep well. Anyone has similar experience?
I wonder if you could make some changes in your bedroom so you would be able to leave him there with a video monitor. Some cosleepers I know only have a mattress so the child can not fall from high. We always put DD in her own bed and moved her with us when we went to bed. I was afraid to leave her alone on our bed to sleep. Maybe try a pack and play in your room. She also had a horrible time trying to fall at sleep if we were there. Alone there would be nobody to play with. If he likes books you could tell him if he stays alone he can have some books with him. DD has always enjoyed reading books alone before sleeping.
Oh and try to cut the milk completely, when our pediatrician told us to stop giving any milk during night or in the bed our nights got much better. If she asked for somethings she got water. If we gave milk one time our nights would be horrible for a week. She would remember it and use it as a an excuse to not to sleep. After getting rid of the milk she did not have that much reason to wake up. We gave her a snack just before going to bed which included milk in a sippy or a cup.