1. Not sure as ours is not a pillow top. How soft is it? Maybe you could put something on top of it, under the sheet, to make it a little firmer? Wool blanket maybe? Not sure.
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2. Been thinking about sidecarring our crib, too and we don't have handles either. My plan is to get some rope, like clothesline, and make a tight loop with it to attach the bungy cords to. Haven't tried this yet though. I'm not sure if just shoving the crib against the wall would be enough, because the mattress could potentially get pushed in the other direction, leaving a gap. Honestly gaps scare me a lot more than soft mattresses or blankets or pillows.
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3. Oh yes, mine got much more wiggly after six months!! Our bed is on the floor, but still on the box spring (but we have a low profile box spring so it's about half as tall as a normal one). The bed is pushed into the corner, and I put a body pillow along the exposed side, and then just listen very closely to the baby monitor. DS's personality is that he does not like to be left alone though, so this works. When he wakes up he just cries until I get him. If he was more the type to play quietly when he woke up I would worry about it more as he might get into something before I had the chance to get him.
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4. DS is getting his top 2 teeth right now and he does cry out some, but usually only for a few minutes. Then I can get him to nurse and go back to sleep.
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5. My DS is 10.5 months and we are starting the slow process of stopping now. He likes to sleep nestled under my arm and he is just too darn tall. I wake up with horrible pain in my arms because he's nudged them up to the North Pole in his sleep. This is why we are sidecarring the crib - I'm hoping to get him used to sleeping in a somewhat seperate space, and then eventually in a crib in our room, and then eventually his own room. (Honestly, I could care less if he stayed in our room but he's a light sleeper so I think he'll do better in his own room - he likes it quiet, and DH and I both snore periodically.) I have heard from other mothers that they were comfortable cosleeping the first year but found it more disruptive after that, while others continued to cosleep with no problem up to preschool age.
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I hope that is somewhat helpful! Good luck!