Jess you are doing a great job, if he wants a cuddle give him one. Hamish is around the same age and he is a fantastic sleeper and i know when i put him in he usually doesn't need settling but sometimes he will have a little sook and i will go put his dummy in but i can usually tell if i have been in there more than twice and he is crying he needs a cuddle as if he is too upset there is no getting him to sleep, but by picking him up usually within a few minutes he is asleep and i return him to the cot. I just go with the flow and let my instincts tell me if he needs settling. Good luck.