Wow. I just put Ben down for another nap. I fed him first, so he was very sleepy. I woke him up a bit so he'd realize he was being put in his crib. (I think that's one reason he cries when he wakes up--he doesn't know where he is) He started to cry, and I braced myself for another 20 minutes of crying before sleep. Ahh...nope. He cried THREE MINUTES. Then passed out! I am so excited about this! Going to try it again at bedtime tonight. All signs point toward him simply being ready for this.
I also wanted to list the differences between his nap earlier, where he cried himself to sleep, (referred to as Today)and his usual naps, where we walk him to sleep, (referred to as Usual) then carefully put him down, sometimes unsuccessfully. If he did wake up, the whole process started over, though often taking less time.
1. Usual- takes him 10-40 minutes to fall asleep, either by eating, being walked, or laying on the bed with him. Today- 20 minutes in his crib, then 3.
2. Usual- If he stirs at all during his nap, that's it, he's awake. Today- he stirred, moved around a bit, then fell back asleep about 40 minutes in.
3. Usual -nap is about 45 minutes long, and he wakes up crying. Today -first nap was almost an hour and a half, and he woke up calmly.
4. Usual -he's still tired after his nap, because he didn't sleep long enough. Today - he was cheerful and awake, because he slept longer.
The other way he naps is on me. That way he sleeps long enough, but I can't get anything done.
I feel so much better about letting him cry earlier! I still don't want to let him get desperate in the future, but it looks promising. I hold no hope for this helping him sleep through the night, or even wake up less, but this will help us establish a usual bedtime for him, instead of whenever we feel up to going through the long process.