Thanks for the responses - and the kindness Rosemary & T.
Yes, looking back at my list I can see it seems quite 'faffy' - I was probably not necessarily intending to do all of them, just that these were my ideas.
I definitely agree that my eventual target is 'good night' and lights out, but am probably looking for an intermediate step to get there.
He does have quite a good routine already. Change (bath if having one that night), into nightclothes, toothbrush, calm down with some books then to sleep (with a bfeed). I am fairly 'attachment' based in my parenting style, however he has almost always slept in a cot and went into his own room from nine months. I have been quite happy bf to sleep and I think the fact that he sleeps through is also a good sign - if he wakes in the night he usually re-settles himself within a minute or so.. However, I know that if I were to then just pop him in the cot without any preamble he would be horrified and just stand there totally frantic. :(
Re the cot sides - I am not too worried about him falling out as the drop is small, though he does sometimes sleep pressed up against the bars. I thought that the small bed-guard might discourage wandering!
A night light is a good idea. Or possibly leaving the door open?
What do you think would be a good intermediate step from where I am now to where I want to be?