Please help. My little man is pretty awesome, but bedtime and sleep in general are a living hell. I have never managed to get him to settle to sleep at night without either a) taking him for a drive or b) standing up holding him in a very quiet room until he dozes off. At the moment this means bedtime can take up to an hour and a half, and nap times are all over the place. Plus my back is killing me.
After eventually dropping off he wakes at least once in the evening and at least once at night, probably because he is dependent on me being there to get off to sleep. I resorted to trying controlled crying when he was 9 months old on the advice of my heath visitor, because at that point he was waking every 30-40 minutes all night. Thankfully that hideous phase passed after a few nights of letting him cry, but I found myself unable to stay with the approach longer term because it didn't sit comfortably with me at all (and often he would make himself sick, which was distressing for both of us).
We follow a bedtime routine where he has his dinner, then a bath, then pjs, stories and then milk before I take him to bed.
Any advice would be hugely appreciated.