Ugh, Maverick Keeps Waking Me Up At Night :(?

I personally would let him be on his belly if he roles there, have you tried waiting out the crying? If that doesnt work put him in his carseat correctly (make sure the harness is on correctly) and try that a few nights and slowly get him back to his bed after a couple of days. Have you tried placing foam padding on either side of him so he cant role over (remember babies should be sleeping on their sides or upright to prevent SIDS-the inability to breathe on their tummies or the sufocation of spit up while they are on their backs)? You may want to let the swaddling go also, it could end up being a very bad thing in the end.