I have my daughter on a pretty tight night-time routine. We change her, give her a quick little rub down, she gets a bottle, then off to bed. Thanks to this routine bedtimes are never hard. However, I noticed that all my husband & I have to do to throw that off is pick her up when she wakes up ONE TIME! If we do that then every night she will wake up after sleepign for a little while & cry until one of us picks her up. So, what i've had to do if either of us ever forgets & picks her up @ night when she wakes up is basically retrain her to get her to go to sleep on her own again. I have to let her cry. But, i do it in a nice way. I let her cry for 5 minutes, go in & comfort her, let her cry for 10 minutes, go in & comfort, 15/comfort, 20/comfort, etc until she falls asleep on her own. I usually only have to do that one night & she is back on schedule but starting out it might take you 3 or 4 nights maybe even longer to get your son on track since he's used to waking up & playing. As for wanting to be swaddled.. I dont really see a problem with that if he likes it.. whats the harm in it? Seems like a comfort thing. I dont really have any advice about that one haha Good luck!