I am tandem nursing and deal with a lot of night nursing here. More that I would like, for sure. I do think the Pantley pull-off technique does help. It takes a lot of patience, for sure, but it is so nice when it finally clicks.
I hear you on the cry-it-out. I tried it once, (not with ds alone, but with dh holding him, in another bed) and after three hours of almost non-stop crying, I decided it was not worth it.
Hugs to you mama, I know it is rough. I just keep telling myself, "he will not be doing this when he is 16." !