What would happen if you let him fall asleep on you, and then transferred him to his bed/cot? What are his naps like during the day? Are they too long?
My son (18 mo) is needy and we have always struggled with bedtimes. He has only once led down awake in bed, and fell asleep with me led next to him.
We have never done cry it out/controlled crying, as he didnt like sleeping a cot, and my partner didnt like to leave him crying. (I on the other hand will defo do it if we have another!)
Occasionally he is up until 9/10pm as he doesnt have a set routine or bed time! What I have found, is moving his tea time earlier, and also limiting his nap to only 1/2 hour or 45 mins in the day seems to make him tired in the evenings. So he eats tea around 5 or 5.30, have a bath, have a light snack after a bath with a bottle of milk, and I just sit and let him fall asleep on me, before taking him to him bedroom and putting him in his bed. This can be between 7 and 8, that he actually falls asleep. It took also a long time to have the evening back, as often he would go down for the 45 min cycle, and them wake up -sometimes hysterical- we would pop in his room, give him some more bottle and settle him back to sleep and repeat if needed. A camera is very useful, I didnt want to spend too much money as alot of them are over £100, however on Amazon you can get some really good deals, ours was only £30 and hooks up to an app on our phones.
Another point to think about is the room temperature. I know alot of babies are in gro bags and very warm- however my boy enjoys no covers and being only in short pjamas- any more and he sweats and wakes up.
As I said above its took a very long time to get to this happy medium, and actually it does not happen every single night! On the days when I work and hes at nursery or with family, he naps more and therefore is up til 9/10pm. In that instance he is downstairs with us playing - Ive had one too many evening spending hours and hours trying to get him to settle, and I would rather let him play and spend the energy.
I thought my boy would never settle in the evenings and have a proper bedtime, so I understand the frustrations!! But just keep looking forward and thinking- its not forever! x