your the mum of your bub and you know best. this is just my experiences so far

dd is a feed, change, play, change cuddle sleep, bub. as my second i generally don't feed to sleep and try to put her down before she really goes to sleep, but rules are made to be broken and I am flexible.

DS is 3 now, and was feed, play etc feed sleep, always fell asleep while feeding. now he is obsessed with skin to skin contact, when he is tired he reaches for anyone's tummy to touch. even when I put him to bed he has to touch some part of my skin while I read to him, we are down to an ankle or hand, and for me this is a win, but we are not quite there yet.

both my cildren are allowed dummies for sleep (have experienced no nipple confusion) ds will be gone within the next 12 months fingers crossed, and I do try to put dd down without hers, but it helps me wit the comfort sucking