Somehow I did this with my DD (age 3.5 yrs) without too much fuss...but my DS won't have it...I wait until he is obviously tired and lay down, snuggling with him and nursing...but.he.will.not.go.to.sleep! argh! he will nurse, sit up, nurse, crawl, nurse, try to leave the bed, and on and on and on...until he is exhausted and then he just starts flailing and whining...I give up and put him in the sling and within a minute or two he is out. I have tried the nurse to sleep in sling then slip him out of the sling into the bed and that is a no-go as well. Help! I set the scene right too...dark, no toys around, white noise, same pre-nap routine...What to do? Keep trying and hope he figures it out?? Thanks!
Since he has the comfort and security he needs with you present perhaps he needs motion. My son needed motion in order to fall asleep until he was about 13 months, so I wore him for naps. He now naps in our bed at 18 months but often needs motion to fall asleep. I sit on the end of the bed and nurse him on my lap while jiggling/bouncing my knees. Then once he is asleep we lie down on the bed. Usually I can roll away after he is into his sleep cycle. If he wakes after one sleep cycle I nurse him down again into the next sleep cycle (no motion needed).
I could only get my daughter out of the Ergo for naps once she started fighting napping there, and I think was also fighting sleeping with motion. She was about 15 months. It took 2 hours the first time we tried to nurse to sleep in the bed, and yes, I committed to sticking it through until she fell asleep no matter how long it took. The next day it took 45 minutes. The next couple of days 30, and then she was down in about 15 minutes after that, though I usually had to be lying with her for a bit longer as she drifted down into deep sleep. It was way easier than I thought it would be, honestly, and there wasn't even any tears. But you have to see it all the way through that first time, i think.