I swaddle him always at night and only during the day if he's gotten restless and fussy. My first baby we swaddled nonstop and she was super addicted to it and it was a pain to get her to stop once she could flip on her face in it so I'm hoping to get him used to not being swaddled for hopefully an easier transition. My other DS preferred to not be swaddled so he could roll on his side from about 2.5 weeks so he was easy
DS1 hated to be laid down and would get mad when we swaddled him. It quickly transitioned to cosleeping and no swaddle.
DS2 was a little more tolerant but it didn't seem he had a preference. I remember swaddling him some but we didn't keep it up long.
We have been swaddling DD at night and she sleeps really well in her cosleeper. We also turn our fan on at night so I swaddle for warmth too. I haven't thought about any transition yet. Hopefully she doesn't become dependent on it. She sleeps in the rock-n-play during the day with no swaddle but it's not the same as laying in a crib or other flat surface.
DS didn't like to be swaddled after about the first week.
She is swaddled at night until she comes into bed with me about four or five depending on when I actually fall asleep.