Thanks for your tales. I think I probably need moral support to keep to a strict timed routine. As you say one extra 15 minutes can lead to an extra hour the next night...
I find ds2 is unaware of how he needs to wind down for his own benefit. At the moment we move from one thing to the next in a familiar order. I go away and do something else, then come back to be with him and move him on again.
He is content to be in his room, so that is good. He generally brushes his teeth. So that is good too. It takes repeated requests and saintliness on my part before he does brush his teeth though.
He actually falls asleep while watching YouTube clips on my laptop. He has a wide bed so it is beside him and it just goes dark after he hasn't touched it for a few minutes.
He wants the light on all night, so I do try to turn the dimmer so it is less than 100% brightness.
It can take up to 4 hours. But I get a lot of rest, laptopping, ds1 time and tidying up done in that time. I used to get cross and shout, threaten etc, but apart from Friday night it is peaceful. That's why I started this.
More than the problem for me is the fact that he dislikes my mil or his father putting him to bed because they say good night and leave him and he gets very upset about being unable to have a familiar distraction to help him drop off. So I am the only one to do the whole bedtime routine. Breastfeeding him to sleep as a baby then telling him stories was bliss compared to this. For him too.