Bedtime has become a bit of a nightmare in our house and my 17 mo ds is now also often waking at night, normally around 4, and taking ages to resettle. Previously he had been self settling and sleeping through. The separation anxiety is off the scale so I know this is going to be a tough time in terms of sleep but I'm wondering if shortening his nap might help a bit? On days when we've been out and he's had a shorter nap he has often settled a bit better.
Currently our day looks like:
Wakes between 6 and 7
Nap from around 12.15 until 3 (I usually have to wake him up)
Start bedtime routine 6.30
In bed 7.30
Then about half an hour of crying until he falls asleep about 8.
I sit with him and hold his hand and sing to him until he falls asleep, otherwise he just gets so upset- used to be able to just put him in bed, leave the room and he'd maybe grizzle briefly for a couple of minutes but then fall asleep.