Hi Monica (apologies in advance for the long reply!)
The link about gradual withdrawal is here (ignore the information on WIWO):
Walk In/Walk Out vs. The Gradual Withdrawal Method (HOW TO CHOOSE)In terms of sleep training the easiest context in which to do it is if LO sleeps in their own crib in their own room. But I understand that's not how many families wish to do things, and that's fine, it can just make things a little more difficult. If you still want him in your room, then probably I would aim to have him sleep in his own crib all night, especially when starting up with sleep training. Consistency makes a huge difference to how well LOs respond to sleep training - he won't understand the reasons if sometimes it's ok to be in your bed and sometimes it isn't. If I'm completely honest (and this is based mainly on reading the experience of other mums on this site as I never co-slept) I think to combine sleep training with an intention for LO to sleep in your bed all night will be very difficult as he is likely to continue to depend on your presence to be able to fall asleep even if he isn't rocked or fed.
How do you feel about that?
In terms of his routine is the BT of 8.30pm when you start your bouncing or is that when he falls asleep? Just looking at his routine I would think that potentially he could be a bit overtired (OT) by BT even though his naps are reasonable as he has his longest awake period of the day after his shortest sleep. I would be tempted to push his morning nap a touch later, 15-30 mins, to see if you can get a full 1.5h nap. And then bring his BT a touch earlier e.g. something like
WU 7.30
Nap 11.15/30-1ish
Nap 4-4.45
BT 8pm
The only other thing that I noticed is that you were potentially breastfeeding him to sleep a couple of nights per week? Does he still feed overnight? At his age he doesn't *need* milk in the same way a young baby does - although breastfeeding obviously has benefits as long as you continue, milk is actually only a drink once they are over one and all of their nutritional needs can be met by solid food, with drinks of other things e.g. water.
All of the above said my suggestions would be:
Start with the first nap of the day and then continue from there
Do a short winddown routine, it can include some bouncing if you wish to get LO calm but not drowsy or closing his eyes
Lie him down in the crib fully awake
Say a sleep phrase e.g. It's just sleep time, you're going to sleep
Sit down next to his crib
If he stands up/cries/fusses just calmly tell him to lie down and repeat your sleep phrase
Stay right with him until he falls asleep
For naps try for 45 minutes and then give both of you a break
On the first day or two he will almost certainly skip naps - that's ok, don't worry and don't try to prevent OT by resorting to your usual props. You can go for a super early BT if he skips all naps.
At bedtime you stick it out for as long as he takes to fall asleep, no break after 45 mins, and the same at night wakings.
At his age you could cut out all night feeds cold turkey as he doesn't need them from a nutritional point of view. But if you feel that's too much change all at once you could set some times e.g. 11pm and 5am and say you will feed him at those times but no other wakings.
Once he is going to sleep in his crib with you next to him, you can use gradual withdrawal to move further from the crib and eventually out of the room.
What do you think?