I am willing to admit that we may have created a monster. DS (now 8 months) has been cosleeping with me at night since 4.5months (a response to the "I really can't take this anymore" hourly wakings during the 4month sleep regression) and only began to be able to take naps longer than 35min in his crib at 5.5months. He sleeps in a Zippadeezip at night and over the last month we've managed to get him down in his crib for the first few hours every night., though he still requires some assistance connecting sleep cycles). So, anyway, DS is rolling, sitting, crawling, and pulling to stand...at at this point is soothed by wearing a swaddle-up (from Love to Dream) for naps and will ONLY go/stay asleep in his crib if he's on his belly. Putting him down anything less than exhausted or attempting naps in the Zippadeezip results in an extended roll- and wiggle-fest and he will not infrequently knock into the crib slats. I know I can't swaddle him forever...but he's so very mobile and so disinclined to wind down on his own. 
Has anyone else been in the position of trying to swaddle-wean at this age or older? Suggestions???
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I'm just swaddle weaning my babe, but she is only 4 months old so I can't really compare. I've just gone cold turkey with her and it has been a bit challenging, but all I can suggest is that if you are using the Love to Dream swaddles, they do come in a 50/50 zip off sleeve. It would maybe feel like the same swaddle to your baby, but with one arm out, and then both arms out until he is used to it - then its just a normal sleep sack. I used that method for my first baby.
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We swaddled our baby for so long. And coslept eventually by choice, it wasn't our plan but it worked for us and the baby and we ended up loving it! But I would basically swaddle one arm in, with legs out, just to give a little feeling of coziness and security while being safe if he turned. And eventually he didn't need it!
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Is the rolling/crawling/pulling to stand recent? I ask, because I remember a few rough weeks where that was all LO wanted to do. Once she got used to doing that (lots of practise during the day), the nighttime schenanagans stopped. So you might consider waiting a few weeks to stop with the swaddle-up (cool product, btw) and try again.
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Yep. We had to sort of Ferber/Weissbluth train DS's naps. They were a hot mess. But now he loves nap.
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If swaddling works for you, I would keep doing it, as long as it feels safe to you. We swaddled our first until 16 months. She loved it. When we stopped we just swaddled one arm and then stopped, and by that age she was fine. PRobably cuz she would get out of it within minutes every night anyways. Even after we stopped she would ask to put her arms straight by her sides when we held her before we put her in her crib. She didn't need it of course, she could get out of it within 10 minutes but she just fell asleep so well with it. We could've gotten rid of it MUCH earlier but we chose not to mess with something that was working so well for us.
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@FliegepilzHut: oh man, I'm all for ditching the swaddles by that point. My favorite sleep book discusses how it's a process for babies learning to get into their favorite sleep position, but it's great when they can do it. My daughter would roll and roll and roll. We were highly entertained watching on the monitor. Tummy sleeping is awesome. She still bumps her head from time to time and it's no big deal.
When making transitions with sleep, I realized I would be so nervous that it was going to be a disaster, and I'm sure she picked up those vibes. I had to try the "fake it till you make it" approach. I would examine the rest of your sleep routine and figure out what is and what isn't working for you, then make a plan. You both can do it!
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Hmm this might be a long shot but for us getting them to sleep before they were dead tired was the key to success. Both my kids (especially my younger one) are belly sleepers. She was swaddled for a really long time too (6m) because she loved to play with her hands. With her it worked to get her to her crib as soon as she started acting tired (for her the sign was that she was suddenly unhappy/whining without a paci) and zipped her in her zippy. She would then take her paci and roll over. When she was just a little more tired she would have a lot of trouble going to sleep.
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@Grace: The crawling is just the last couple of weeks...hasn't pulled to stand in the crib yet. But I bet you're right that the new skills are at least part of our problem.
@gracecat: He's definitely safe! But I'm hoping I can get him in the less-restrictive Zipadee-zip for naps if for no other reason that it keeps his hands out of his face.
@Happygal: At what age was your LO rolling around so much? When my guy first started rolling, he would swing over *hard* and invariably knock his head.
Now he'll roll and sit up, and if he's not ready, he just WON'T. GO. DOWN. But I'm still worried about him doing near- daily headers into the sides/slats of the crib...which is why it's so hard for me to get out of his room and let him figure it out! 
Thank you for the (much-needed!) pep talk and solid advice. We are in the midst of a somewhat slow and incremental transition from only sleeping in arms to more and more independent sleep. Change is hard but I'm a definite believer in "faking it" until you make it! BTW-- which is your favorite sleep book (I feel like I've read/am currently reading most of them!)?@Pumuckl: Certainly seems worth a try, although his wake time of 3-3.5 hours before bed seems pretty appropriate. So hard to pick out patterns and determine what is/isn't working at times...!
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@FliegepilzHut: hmm...so much of sleep stuff is a blur! I believe the rolling was earlier, like 6 months or so? Whenever she was easily doing 360 rolls, which took her a little longer. I think around 8 months or so, she started pulling up. We put the Pack n' Play to good use at that time (I thought it was a bit of a waste at first). She spent a lot of time practicing pulling up, sitting down, rolling around. It was work for her. I felt like I had this WWF baby in the rings. Even now, I find that she likes to sleep near the edges of her crib. I think it must be comforting for her.
TheZipadee-zip is a godsend for many people and I hope it can help you out, too. We tried it just for a few nights, but my daughter likes to have her hands free. I noticed she likes to bat at her ears for comfort, and by that time, she had a stuffed animal she liked to play with to help her fall asleep.
I LOVE the book "The Happy Sleeper." The tone is so reassuring and straightforward. The first line is "Your baby already knows how to sleep." That was so helpful to me and I realized at one point that I was getting in her way of falling asleep. Full disclaimer though--we did not do the sleep training section for the older baby, which I think is like the Ferber method (frequent check ins with limited interaction). But all of the beginning recommendations are things we've done that have seemed to help. There's a trouble shooting section as well.
Keep us updated! I'm definitely no sleep expert, and we advanced slowly to getting through the night. But I like thinking about things and trying to trouble shoot with others.
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@Happygal: Thank you! I read (and liked!) The Happy Sleeper... Sleep is so hard...but I think we are making serious headway. The biggest advantage to the Zipadeezip seems to be that it keeps his sharp little nails out of his face while he's sleepily rubbing his eyes.,, I will keep you posted as we progress!
Now he'll roll and sit up, and if he's not ready, he just WON'T. GO. DOWN. But I'm still worried about him doing near- daily headers into the sides/slats of the crib...which is why it's so hard for me to get out of his room and let him figure it out! 
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