We did similar to Artechim. DS1 has never self settled for us. He goes to sleep as soon as his head hits the pillow at day-care but at home refused. As baby we held/cuddled transferred as he got older he would fall asleep on the couch. DS2 was born when DS1 was 2.6yo & has never been a good sleeper & I just couldn't cope with both boys up to 10:30 -11pm slowly getting later as DS1 was more taken with the TV and music etc. One day out of exhaustion I cracked it & now both boys (after a spell at sleep school with DS2 when he was 4 months) have the same routine dinner between 5-6, bath 6-6:30, wind down with milk, books & a few wiggle songs & bed for 7pm. If DS1 has been allowed to sleep at day-care we struggle but generally he now knows he is tired. We still have to lye next to him but we know that he will let us know when he is ready to do it alone.

I know it's hard but to break that cycle you will probably need to put up with a cranky DD for a couple of days. I would plan activities for those days. I found DS1 was better if we were not in the house and had other things/people to occupy him. I also know how daunting that sounds as for a few weeks after moving house (DS2 was 8weeks when we moved) DH & I talked about what we were going to do as we had no time for ourselves. The night I cracked it we decided that at night DH was responsible for getting DS1 into bed at 7pm (unless DS1 specifically asked for me) while I worked with DS2. There was much protesting & crying even with us lying next to him but we gently consoled him, explained, listened to his worries.

Huge huge hugs sleep is the one thing I found & still find hard to teach my children. As a child & up to being 11yo I was a terrible sleeper also. Now I can't get enough ;-)