Short version: Do we just rip the band-aid off and swaddle wean while transitioning him from the RnP to the crib?

DS is 4 months and 1 week and can now maneuver himself onto his side in the RnP. We're biting the bullet and transitioning him to the crib now, which is elevated with a crib wedge. He's been napping in the crib for the last month (swaddled with 1 arm out) and naps in a crib at daycare (they don't swaddle him, but I think they use the swing to get him to sleep before moving him). He has never been a good night sleeper, but it's been much worse in the last month. We figure we might as well go all out with the transition and swaddle weaning together because we don't want to have two transitions from hell when we can just go with 1 (if it works...).

Would you:
1. Transition to the crib while still swaddled, and then once the dust settles move onto swaddle weaning?
2. Move to crib and swaddle wean at the same time?

(Yes, all of my posts recently have been about sleep and cribs, it consumes our life and we're ready to move on!)