Prepare yourself for maybe more information than you wanted:
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I want to be clear about what you want: you still want to be in a co-sleeping situation, but you want bedtime to be an easier process?
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Sleep issues are the worst, because when when you're tired you can really start to feel like you're losing control of who you want to be as a parent. When my daughter was having problems going to sleep, there were so many times that I thought, "I don't know how our family is going to survive this!" Now, happily being on the other side of this hill, I look back almost with a hazy amnesia. I assure you, there is light at the end of the tunnel. We were a co-sleeping family and never did CIO and now my 27 month old goes to sleep in minutes and for naptime will read quietly for a few minutes to herself before rolling over to go to sleep.
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So, some things that might help from my bag of tricks:
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Just like you have a breastfeeding relationship with your son, you have a sleep relationship with him, and everyone's opinions need to be heard. I would examine your situation to see if co-sleeping at night is still the optimal situation for you. It may be that after not seeing your dh all day and not having alone time, you need for your sanity (and for your ability to be a happy mom the next morning) to have some pillow talk time at night just the two of you. With the frequent waking and wanting to be awake while you're awake, your son may also be indicating that he might be ready for solo sleeping. In my family, I found that dd started to sleep better in her own bed. She started to think about bedtime as being time just for her, that night time is for sleeping and not for interacting with us. Eventually she even understood the fact that mommy and daddy have things to do after she goes to bed. I can say, "Good night. Mommy needs to go do laundry, but I'll check on you later," and she's fine with that. This did take time, and she is 6 months older than your ds. We did have to get to this point.
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For a long time, we had to sneak out of the room with dd. Or if she was nursing to sleep, I would have to unlatch once she was completely asleep and then tip toe away from the bed, praying she wouldn't wake up. I realized that sneaking out of the room defeats the idea of getting her to fall asleep easier, because then if she did awake, not only was she awake, but she was angry that I wasn't where she wanted me to be. So, the goal because to be able to leave the room while she was still awake and a big portion of this was not nursing to sleep.
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I read The No-Cry Nap Solution Book, which has a lot of the same ideas as the No-Cry Sleep Solution Book. Â It touted the importance of routine, routine, routine, and that has certainly worked with us. Â I started by being stricter about what time she was going to head to bed every night. Â Then, I made sure to have a bit of a routine so it just wasn't nursing to sleep. Â The book pointed out that if you only nurse to sleep that nursing is both the sleep aide and the sleep time indicator. Â
To start our routine, we do diaper change and pajamas then we brush her teeth and wash her face. In the beginning, I would read her two books in bed then I started to nurse her while I sang three songs. Â During these three songs, I didn't care if she was kicking the covers or rolling around; she can do whatever she wants to get herself in a mood to sleep, and I don't allow myself to become frustrated during this time that she isn't sleeping. Â Once the three songs are up, then I do expect her to settle down, and if she starts to crawl or sit up, I ask her to lie down. Â She's usually pretty quiet by this time though. Â
In the beginning when we started the routine, I would rub her back during this quiet time while she nursed until she fell asleep.  After a few days of doing this routine, after the three songs, she would just roll over and go to sleep.  After a month and half, she wouldn't wait that long. Then, I started to read a story or two, maybe sing one song in while she's nursing, then she would roll over to go to sleep or to let me rub her back asleep. A few weeks later, she even let other people put her down to sleep by just singing and rubbing her back (and not just with Daddy either, with visiting grandparents and a family friend).
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I eventually modified this routine so that we were nursing less by instituting a nursing count down. Once we got to only nursing for ten seconds, it wasn't that important of a part of our routine, and Dad could do bedtime all of the time. If your ds and you still want to nurse before bed, maybe you could do that downstairs before dh takes him up for bedtime. (You can get dh to take over bedtime by having him gradually adopt each step: "Tonight, Daddy's going to brush your teeth." "Tonight, Daddy's going to read your stories.")
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Sorry to skip around so much, but my mind is a bit crazy with two kids to deal with, so, back to sneaking out. The book had good advice about this. It recommended that once you get to where your child is happy somewhat falling asleep without nursing, then you start the end of your routine next to them (for us, this would be singing), then you gradually move further away over a period of time until you are eventually outside of the door. This took a while for us--it's certainly a process--but we can now sing a song on our way out of her room. And now, if she calls to us after we're gone, she's accept it if we call up to her to close her eyes. She's also to a point where she can talk to herself for a few minutes before falling asleep.
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We still have some nights where bedtime is rough and my dh will need to lie next to her for her to fall asleep, but these nights are few and far between. Building a solid routine that gradually put the focus on her falling asleep unaided was what really helped us. Now that we're over sleep issues, I feel so much better about her, my parenting ability, and our future as a family. She's only six months older than your ds (and has been doing this for a few months), so there is a light at the end of your tunnel that is just around the corner.
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I hope something in this mess was helpful.