Some kids are wired differently. Let me tell you about my oldest and you can see if it relates to you, and your situation. He never slept in his crib, always wanted to play, never seemed to want to go to sleep, even when I knew he was sleepy. He slept in a swing...until he was two. I used to let him fall asleep in it;then move him. My theory was, at least he was sleeping and was getting used to napping at certain times. Really what is the problem with letting him nap in a swing?
If you are adamant about moving him, try it this way. Put a sound machine in his room. Get him used to the sound for a few days. Do not try to move him yet. Then after the 5/6 day, give him time to fall asleep (20 mins) then move him. Keep his room cool and very dark at all times. My oldest was very stimulated by light; we had to make his room black. (He is 12 now and sleeps with one of those eye covers) If he wakes up, start all over. If he continues to wake up every time you move him, wait another 4-5 days and start all over. Give him time to get used to the cool and machine. All mine napped in the swing (I have 4) I did this with all of them, It was hardest with my oldest; probably because I was not as consistent, and was influenced by others opinions. Other three napped in swing till 1 yearish, then I did routine with them, and they were in bed ( until they got a cold or something, swing helped them breathe cause they were propped up and was soothing)
It is also not "your fault". Your child is a child and you do whatever works to make your household run smoothly . If he napped in a swing, and you were a better mother for it because you got to rest or whatever, that is the way it is. No apologies or blame. We all do our best and we as mothers need to stop beating ourselves up for things that we cannot change. He calmed down, you said. That is more important. Some kids don't self-soothe as easily as others. You are doing better by teaching him that there are ways to calm down than to let him be frustrated. To this day, 3 out of 4 of my boys will rock themselves when they are tired. They all say it makes them fell better. Maybe that is just what he needs.
Good luck. Let me know if you need to anything else I did.
L.