We swaddled our son until he was about 6 months old. We used oversized flannel swaddling blankets up until then. Around that time, he was able to squirm his way out of the blankets because of his size and strength. I had wanted to switch to a swaddle me or something of the sort, but he was too big for that too. We decided to go cold turkey on the swaddling because we found him one morning with the blanket over his face.
Around the same time, I discovered a sleep sack that had long sleeves and hand covers (our son was swaddled because along with startling, he was a face scratcher and hair puller). We started using the sleep sacks, and I rocked him all the way to sleep - until he was soundly asleep. After a week or so of that, I rocked him only until he was lightly asleep, and then laid him in his crib, and rubbed his back (after we removed the swaddle, he slept best on his side). After a week of that, I started laying him down when he was almost asleep, and then another week later, I laid him down fully awake, and rubbed his back if needed. Now, he'll celebrate his first birthday on Sunday, and he gets laid down fully awake and needs no extra soothing - he just falls asleep on his own. He does have paci's though, and I usually put four or so of them in the bed with him, and he reaches for them and holds them as he falls asleep.
We're not comfortable letting our son CIO, so this worked well for us. It took some time, but it was gentle for him, and felt right to us. When we woke during the night, I would go in, rock him to the same level of sleepiness that I was rocking him at bedtime. He no longer wakes at night, and on the off chance he does, he goes back to sleep on his own. The only reason I can tell he's woken is because his breathing changes. (He's in his own room, but we usually have the monitor turned up pretty high).
Good luck!