DS is almost 18mo and has always needed a bit of help falling to sleep at bedtime. On a good day I can sit in a chair in his room by his door, with my back turned and very still, and he'll happily fall asleep on his own. On a normal night he wants to hold my finger, so I have to sit closer so he can hold my hand through the bars. Sometimes he'll stand up and have one last hug over the side, before he sits down again, and he might do this a few times. On a bad night he needs a bit more help - more hugs, patting, rocking etc.
Mostly, this set up isn't too bad. It keeps him happy, and it takes about 20-30 mins. We just accept it, and it means at least he goes to sleep without tears and we can get on with out evening.
On the nights where it takes longer, or he starts messing around and takes ages to drop off, I feel so angry that I have to spend my evening in his room! We've tried gradual retreat in the past and got as far as sitting outside his room, but there is always something that sets us back - illness, teeth, weekend away etc.
I know he'll eventually grow out of it or change or just get older and I can talk to him and tell him I'll be outside/downstairs if he needs me etc and hopefully I'll be able to leave him awake. So on a good day I'm happy to just do what we do and just accept that this is what he needs.
But then I wonder if I'm doing him no favours by not 'teaching' him to fall asleep happily on his own in his room. Am I denying him an important life skill by holding his hand/rocking him etc??
Paranoid mum here, tell me It'll All Be Ok In The End...!!