We have reached the point where we need to sleep train DS (14 months) from breastfeeding to sleep. He gets very worked up (hysterical) if we put him in his cot awake to the point where he will stand up and scream and scream. Drowsy but awake has always been elusive. He seems to be awake or asleep without any snuggly between stage. I get him to sleep by him lying beside me in our bed and feeding and I carry him to his cot when he’s asleep. He’s much harder to transfer back once he wakes up in the night.
I tried a form of verbal reassurance last night. He woke after six hours (woohoo!), I fed him and put him back and kept coming back into the room after a minute or two to tell him it’s time for sleep. It seemed to work initially and for nearly an hour he seemed to keep getting near sleep but he never managed to completely drift off and then after an hour got very upset, standing up and undoing/popping out of his sleeping bag. So I gave in and he came to sleep with us.
I accept he may continue to wake at night and I’m happy to continue to feed and I’m happy to co-sleep for the last stretch of the night (though that may be confusing) but I really need someone else to be able to put him to bed.
Getting him to go to sleep for a nap is the most important change I’d like to see and I know people often say to start with naps but I’ve no idea how that’s even possible as if he gets upset at nap time then he’ll just wake up and not nap at all. He’s on two naps at the moment and I know we’ll likely need to transition to one nap soon and maybe we should start there? He’s always had more of a rhythm than a strict routine and naps roughly 3 hours after waking and then 3 hours after the first nap which can sometimes be a bit late.
Can anyone help us?? Do we need to commit to verbal reassurance or another technique? How upset is too upset? 
Oh and one final thing is we live in a flat and worry about the neighbours. We’re away next week. Should we sleep train when we’re away or is that a mistake because we’re all out of our routine and he’ll be in a travel cot which he doesn’t enjoy?