We ditched the wrap the first time around at about 3 months I think. We just went cold turkey and DS didn't really notice the difference. We started again, believe it or not, when he was around 6 months and did it for another month. He began to roll over in the cot and the rolling coincided with taking a long time to get to sleep. The swaddling helped for about a month and then he worked out how to worm his way out of it. We swaddled in a cot sheet at 6 months as he was too big for his wraps.
DD stayed wrapped until she was 1 maybe even a little older. We went cold turkey after a few days of finding her completely out of it.
In the warmer weather we only used the Muslin wraps. Depending on how hot the nursery got would dependon what clothers we had on her. Really warm nights were just the singlet bodysuits and wrap.
another thing you could look into is a relatively new product called Sleepy Wings. These canbe used with or without growbags. I have no idea how good they are as I am yet to try them out but in theory I think they are a great alternative to swaddling.
DS is still swaddled. We tried him without it around 5 months, and it seemed ok for a couple of weeks but then he started waking every hour and it was back to swaddling! He's in a sleeping bag now, and we use muslin wraps. He gets one arm out and sleeps like that. Weirdly, he doesn't sleep well if he has both arms tucked in, and if we unswaddle him he wakes up in a few seconds. If he moves his arms he gets out of the swaddle completely, so the swaddle is really just a gesture, but he likes it. When he wakes up he rolls and the swaddle comes undone, so that doesn't bother me. When he starts to want both hands out we'll ditch the swaddle.
Your DS would tell you if he flipped over and got stuck, but maybe you could not swaddle him very tightly (if you decide to ditch the woombie) so he can move his arms if he rolls?
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