Haven't done it with a newborn, but you can try lying down with both of them, feeding a newborn while sitting with older child, wearing newborn in a sling while helping older child to settle, etc.
About 2.5 I think every other night, depending on how she felt, every night by 3 years.
TBH I would still be in there at the end of her bed I think if I didn't have to deal with feeding and settling DD2. DD1 still asks me to sit with her a while, but it is only a few minutes and then she is happy to fall asleep alone if she isn't already.
Haven't yet. DS is 3yrs 3 months and we read him two books (DH one, me the other) and then either one or both of us lay with him while he falls asleep. If we attempt to leave before he falls asleep he gets upset and calls us back, so we stay. I have no intention of changing this until he leads the change (and now we just bring DD into his room and she is now part of this routine). I love his sleepy cuddles as much as he wants us there, soon enough he'll be all grown up and wont need/want us there, but for now it works for all of us
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