I do miss having my own car, but on the plus side it's good for DS's routine, plus the less I go out the less money I spend! LOL We live in a big city, too many places to go and spend money!
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My DS always did (and still does) best with a slightly shorter A to bed. Actually, what worked was a shorter morning A, longer pm A, then back to a shorter bedtime A. Not a lot shorter, just whatever you can manage. I understand not wanting him in bed before 6:30, that is my cutoff too. And I don't think a catnap is the solution either.
At this point you might just need to ride out the post-bedtime NWings, like you said it only lasts until 10 and he goes back to sleep easily. It could be too much noise, it could be he needs more sleep maturing. Obviously you've done a lot of tweaking and they are still there! I could never figure them out either, those sorts of phases would just come and go but one day they did end.
I think I've asked this before, but will he settle on his own? Maybe if you can leave him to it he'll get the picture and will stop waking so much when he realizes that you're not going to help him back to sleep. I found with my LO I spent a lot of time figuring out what kind of crying was ok, and then letting him learn to resettle on his own. I realized that even a loud cry isn't necessarily an "I need you" cry, and I could leave him maybe up to 15mins and he'd eventually resettle. The more I left him to it, the less he woke. The point is, it's ok if they're waking often, that's just what happens. What you want is for them to put themselves back to sleep. Maybe he just needs more practice.
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