I would. I swaddled DD from her chest down (she sucks on her hands instead of a paci) and also had her in a sleep positioner. When she rolled and moved the sleep positioner, I knew it was time to quit.... it has been a rough 2 nights with 2 wake ups each night as opposed to her normal 8-10 hours straight. I figure she'll get the hang of it soon and resume her normal sleeping.
Yes! It is important to stop when LO can roll over, especially when he is rolling onto his tummy while swaddled. I have found weaning gradually to work well, but in your case, it'd be best to go straight to a sleepsack. Halo Sleepsacks are great!
Re: Should I stop swaddling?