I too wish to send you good luck vibes.
I think you've picked the perfict time to start. Your LO is old enough to sleep by himself, but young enough to make the trasition easier.
I agree about the swaddleing, it'll really help him feel more snug and sucure. You could even use a blanket that you and your DH have had in the bed with you, so it smells like you, Not sure if it'll make a big difference, but it might, the pillow idea made me a bit weary.