Not sure if this answers your questions, but I just started feeding dd earlier in our winddown routine so that it wasn't the very last thing before sleep. We started out with naps, and then when that was going well, did the same for night.
Has your lo ever gone to sleep without the breast? I'm not sure how well our method would have worked in that situation, but for us it wasn't an all the time habit, so we did know that she was capable of going to sleep without it.
You will surely get some protest, which means you're going to need some sort of game plan of how you are going to handle getting her to sleep. That will jsut depend on what you are comfortable with and what works with your lo.
~Kim