Baby sleeping situation

Heeeellllppp! Our baby is almost 5 months old, we have spoiled him by letting him take naps on our laps and chest. When I try to let him down on the bed I take it slow, shush, hold the pacifier and wait... maybe 10 minutes later he wakes up. I also want to get him out of a swaddle, but his doggone arms always wake him up. He sleeps in a rock in play in my room, but I want to transition him into a pack and play then to the crib. ALL SUGGESTIONS ARE APPRECIATED!