Your kids didn't loose it totally when you tried to remove the nipple before they were completely asleep? [...] I pretty much have to wait till his jaw muscules relax when he's falling asleep, and he has to know ahead of time it's my intent to do so, or he'll wake up and cry when I move away (even if no part of his mouth is still touching the nipple).
I put these parts together because IIRR a jaw relaxation was part of what I was paying attention to, to know that I wasn't doing it too soon - so it's possible that my "not completely asleep" and your "falling asleep" are the same point actually! It's so long ago I'm not sure, but I think DS's jaw would relax at around the same point when he stopped actually getting milk; and it makes sense that he wouldn't like being interrupted earlier.
I vaguely remember being confused about how this was supposed to work; I've long since given away my copy, but yes, I think she may say something about some crying being OK. I never found an intermediate between "losing it" as you say, which was obviously (to my mind) not what she meant as it wasn't getting him closer to sleep, and no crying at all if I got the timing right. Given the title of the book I was happy with the latter and took it as a sign that I was doing it right! But I think she did present a picture of the baby being taken off, protesting sleepily, being put back on, repeat? We never saw anything like that, though I think I read posts from people who did (I was on a yahoo group that discussed baby sleep including, often, NCSS, at one point - no idea whether it still exists); at any rate I believe it exists.
You say "alone in the dark" - have you experimented with light levels? I did read some stuff about this being bad for eyes, but this was something we gave up on very early; we set the light level to what DS wants. Just recently (he's now 7) he talks about having overcome his nictophobia, if I have the word he uses, so as now to be able to go to sleep in complete darkness (e.g., when we all share a hotel room and it is 2 to 1 wanting darkness!), but he still prefers a low light on.
Do books have a role in your DS's bedtime routine? He's not far off the age that my DS was (2y10m perhaps?) when we added in the "now you can look at books for as long as you like" step, which was how he learned to put himself to sleep. Once he was in bed I'd read 2 books to him, then breastfeed him, take him off as discussed, and if at that point he opened his eyes and looked awake, I'd take it as a sign that he wanted to look at books for a bit, tell him that was fine, make sure he had the ones he wanted (they were typically heaped up around him anyway) and leave. Quite often there would be a shout of "can someone come and lie down with me?" a bit later; generally DH would go. The rule was that someone would lie down with him if he asked (I think this was important in his being willing to let me go in the first place!), but only if he was actually trying to go to sleep - he didn't get the choice of someone to lie down with him while he was reading (or "reading"). Gradually less lying down with him was needed, and less often, and it came to be routine that he'd want to read after the last breastfeed, and they all lived happily ever after. YM, of course, MV.
