Timely question for me personally...
I too have always let DS take the lead with regard to sleep. Until two weeks ago, he had always nursed to sleep. At two, DH and I were starting to make a plan (via our own discussions and having read NCSS) for nightweaning because frankly, I was tired... wearing out. *sigh* Anyway, I had begun singing to him at night and taking him off the breast and rocking him down instead. He was fine with this... however, it had been taking him longer and longer to get to sleep.
Two weeks ago, we'd been at it an hour and he still wasn't asleep. Honestly, I just had this feeling that it would be 'ok' to put him down in his crib. I can't explain it, just one of those amazing cue reading moments and low and behold, I was right. He layed down (didn't pop right up and start crying like in days past) asked for his doggie and blew me a kiss! I walked out of the room in shock and mostly thinking that he would of course starting crying for me any minute. That was two weeks ago, he hasn't called out for me yet. Better yet, since he's been putting himself to sleep, he's only been up once a night (down from three or more). I'm nursing him for now and find this manageable but may eventually night wean entirely... haven't decided.
THe only advice I can give is this: time it right! There were a few things working for us on this one that truly helped: Most important, I waited until he was in a good emotional space... he had recently been through a clingy stage and I waited until he was beyond it and his happy go lucky self. The other things were more him than me... he's been into pretend a lot lately. One of his favorite things is putting his animals down for naps. I think somehow this must have made him start thinking about how others go to sleep (not everyone nurses to sleep, etc). Also, he's becoming attached to his stuffed dog with no urging from me at all. I think it helps that he has a buddy in bed with him. Lastly, for us we are fortunate to have just ended teething...
It's apparent to me that DS is extremely attached to his naptime nursing. I'm not planning to change that. I'm a SAHM so this works for me. My philosophy on this one is that the nap evenutually ends and with it goes the nap time nursing.
Best of luck to you!
Em 43 - Wife to hubby Mom to DS born: Jan. '01