Soon to be kindegartener will not sleep or wake alone

[milkmamamerina]

My ds is 5 in Oct.
We have tried numerous times to ease him into going to sleep on his own by sitting near his bed or giving him 2 minute practices of being alone in his room in bed. During the two minute practices he gets scared and comes crying back to us, and when we have sat in his room but not in his bed, he eventually hoes to sleep, but then acts out all day the following day. Every night my husband or I cuddle him to sleep in his own bed, but he inevitably wakes at some point in the night and joins us in bed. While joining us is not a problem, the sleep interruption does seem to affect him and he refuses to wake up on his own and go play in his room (the doorway is literally a couple inches from ours). This makes for very grumpy mornings since he kicks and squirms against me until I just give up and grumpily get out of bed.--he wakes with the sun despite our black out curtain. He had been a full time family bed sharer up until about a year ago when he got his own bed and bedroom.

So, does this seem to be a bit much? What can we do to help him 1. Fall asleep on his own, 2. Sleep the night through, and 3. Play independently when he wakes up too early for us.
I'm not looking to change these all at once, but I want get on the path toward these goals.

[HappyTomato]

BTDT. It took a while for us but we eventually got there. Keep working on him going to sleep by himself independently. That was the key for us. Be consistent and don't give in. We had a reward system with a chart and stickers for everytime my son would stay in his bed all night. Boost his confidence and be encouraging when he accomplishes a goal. Walk him back to bed everytime he comes into your room. Teach him how to read time and get him a clock for his room. Explain to him that he has to wait until the clock says 6 (or whatever time) before he can come to your room.