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With my kids, if they were down for the night and woke up, it was very rare that they wouldn't quickly settle back to sleep if I went in and laid with them and nursed. With Lorelei I wore her for all her naps until she was about ten months. At nights I would typically hold her and Mr. T and I would talk, or watch something on Netflix and she would sleep through it. Then she went to bed with us. Now, since 12 months, she naps solo on her floor bed, and starts the night there on her own. Then we take her to bed with us when we go to bed. It sounds to me like you have a good plan-- there are lots of different ways to make bed-sharing work! I don't know if I'm answering your question very well or giving enough information, but feel free to ask whatever and I'll do my best to answer.

As for the bedtime, A started going to sleep around 9:30 and over the last two weeks (he's almost 11 weeks) he just started showing tired signs earlier and earlier every couple of days. When we tried to push him and start our routine earlier, it didn't work - even if he fell asleep earlier, he'd wake up and go to bed for real at 9:30.

So, I guess I have no real advice other than to watch the cues. We've gotten pretty good about quickly getting him to bed as soon as we see the tired eyes or yawn. Tonight he decided to put himself to sleep at 8:30. In my opinion, he's still a little early to try and force a schedule.

@Silva: we had similar sleep issues, and it would take FOREVER to get A to sleep, and stay asleep. I feel like one day he just "got it" and there have been times in the last week or so when I just put him down awake and he manages to fall asleep on his own. I swear I haven't done anything different - these babies keep us guessing! Hope you find something that works for you soon

@Silva; yep. Just exactly like that. I would feel comfortable doing it if I had a video monitor or it was a slightly older baby, but I'm paranoid. I just always managed to find other solutions that worked well enough for us that we never went there. The women who mentioned using it used it pretty much from the beginning and never had any problems. I've done the pillow thing, too, though.
ETA; I never did any sort of sleep training or trying to teach my children sleep habits, and they both progressed and learned things on their own. There's nothing wrong with whatever method parents choose, but you can have success even when you aren't actively trying to instill future sleep habits.

@Silva: my little one is only 8 months and we still bed-share. I do the nurse to sleep thing and most of the time I can put her down in the crib or on the bed without her waking. I would hold her for 20-30 minutes or lie down next to her and sneak away after a bit. It took a bunch of times doing that before I could get a decent nap out of her. This was around 6 months.