Healthy Sleep Habits
What really helped DD when she was about 18 months was giving her a fuzzy pillow to sleep with. You could use a blankie or a toy, anything that he gets excited about and reserve it only for bedtime. Maybe make a big deal over going shopping for one and let him pick it out? DD was so excited about her pillow that she would demand I put her in her crib at bedtime, then I would tuck her in and sit beside her crib till she fell asleep. It took about an hour at first and she would bounce around, I just kept reminding her to lie down because it's time to be quiet and she needs to snuggle with her pillow. Then she started falling asleep faster till we were down to 10-15 min. RIght now she's going through a bit of a regression and falling asleep in 30 min again but it's not the worst thing.
Before we did this I would rock DD to sleep, then I started only rocking till she would close her eyes and stop, then stopped earlier and earlier so she would get used to falling asleep without the motion. I think that helped us transition to her falling asleep in her crib. And once she could fall asleep in her crib the number of wakeups reduced dramatically from about 4-5/night to one and sometimes she would even sleep all night. When she awoke I eventually stopped picking her up too, I would just comfort her with her still in the crib. She got upset at first cause she was used to being picked up but I would hug her, rub her back, and reassure her that I was right there and she could go back to sleep.
This was partly based on No Cry Sleep Solution and partly we just winged it because DD got all excited about that pillow. I hope some of this is helpful for you!