I don't see this one come up much - I have a child who used to wake me every couple of hours at night for the breast. I kept trying and finally night weaned him (mostly) at 19 months - but some things never improved. I mean, I am grateful that he (mostly) sleeps through the night now, even though I have some insomnia, but that's another story...
Now he's 2.5 years old, and he doesn't sleep well during naps. On good days, he wakes up once and needs me to help him get back to sleep. On bad days, I pretty much can't leave him. He wakes up several times, or sleeps so lightly I can't leave without him waking. Oh, and I have to breastfeed him to sleep 90% of the time, or he just won't nap.
I tried changing this (read the No Cry Sleep Solution) - I pretty much can't get him off the breast before he's fully asleep or he protests until he is fully upset and not going to nap; I implemented a pre-nap ritual of books, talked to him a lot about lying still and quiet, etc.
When he wakes up, I've tried sitting on the bed away from him, which occasionally works. Reassuring him and walking away, or being in the same room folding laundry, is apparently not good enough.
For bedtime, he always wants to breastfeed before bed. The routine I managed to implement, though, is that he must do so with the light on and not fall asleep there - he finishes falling asleep with the light off, but of course with me right there.
He's always been that "high needs baby," too. I'm just at another point in my life where I am wondering, what did I do wrong? (like so many of you, should I have let him CIO? I think he would have puked) Why can't he have a normal nap without needing me at least once in the middle of it, for 20 minutes or more? What can I do to change this?