I have an 11 mo boy. 4 months ago we bf to sleep (or he wouldn't sleep!). 2 months ago we bf to drowsy but he fell asleep in bed. Now I put him in bed, give him a kiss, and leave the room. For all naps he'll go to sleep by himself, but bedtime is a different story - usually he needs me to sit with my hand on his tummy, though tonight he did actually self-settle. Sleep training really does work!
For nap routines we cuddle in the dark with white noise on for a couple of minutes. Then I pop him in bed. For bedtime he has supper, nappy, story, teeth, and cuddles. he takes half an hour to feed, so the whole thing takes about 45 min until he's IN bed; going to sleep in another matter!
Honestly if he's broken the feed to sleep thing himself that's half your battle. Does he lie in his bed calmly, even if you're in the room? If he does I would just sit with him until he's asleep. I always thought white noise was a waste of time, but it's SOOOO helpful.
For night wakeups, I found feeding an older baby stimulates and leads to more wakes. Do these things:
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Leave baby in cot, but pat his tummy calmly or hold his hand with white noise on. Give him a good 5 min to calm down and evaluate then decide your next move
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Baby still upset - pick him up and rock him to calm down. Again, give a good 5 min of this
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Baby still upset - feed to sleep.
Make a pick up/feed the last thing you try. It won't work every time, but once he starts to settle without feeding it does start getting easier.
Good luck!