Hey there Mamaduck,
My DS is learning to put himself to sleep also. Several months ago, he started putting his stuffed animals down for naps. He'd have them all in our bed, tell them a story and shock, didn't nurse them all before telling them goodnight, snuggling under the covers himself, and pretending to fall asleep.
I don't know how this started, his own idea and also his very own lightbulb popping into his head. I do imagine that he is realizing that Mommy and Daddy sleep, but don't nurse down? *shrug*
Anyway, a few months of this and I decided to give it a whirl. Put him down awake (after nursing and rocking, 25 or so minutes) and after playing around a bit, he fell off to sleep. He was so fine with it that I was totally disconcerted. I think he was just ready. Some nights the playing lasts longer than others (like the night he sang chorus after chorus of U2's Lemon!
) and others, he falls asleep rather quickly. And then, there are still nights when he doesn't want me to leave him until he's alseep. We're taking it a day at a time...
Anyway, the playing thing is a bugger if he can't get to sleeping within a reasonable amount of time. Like you said, it's getting late! I think the story tapes are a great idea. Since he wanted to go to bed from the get go (not a lot of nursing or rocking), maybe he just needs more help "setting the mood" for sleep? I know DS is having a more difficult time these days going from play to sleep... I'm looking into some options myself!
Best of luck!