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I'm curious about the responses! DD sleeps really well in the RNP. I want to transition her at the end of this month after we get back from visiting my family. I'm nervous about screwing up her sleep!

The "when" is sort of whenever you want to bite the bullet. It probably will be tough whenever you try it (hey, you never know maybe he won't have a problem!)

first off, I'd think about whether he goes down easier for night sleep or naps. If its naps sleep, reverse the order of the below steps. I chose to start with night sleep because my lo went down easiest for that to begin with.
1. stop auto rock. maybe try stopping it for night sleep first for a few days. then naps.
2. crib for night sleep. this will be tough. soothe as necessary. odds are good you'll get a nice first long stretch, he wakes and he might not be able to resettle. worst case scenario: back into the RnP! Keep at it, eventually he will sleep through
3. crib for naps. This should be better by the time you implement it, because he'll be all "hey I know what this cage is for". i'd try to leave him in for a good 45 min period (or whatever his nap periods typically are, even if you are in to soothe multiple times. Some people refer to it as the "crib hour".

Do you swaddle? If not, then I wouldn't start unless he just DOESN"T get on board with the crib for a week; he might just need that cosy feeling that the RNP provides. I think getting rid of the swaddle down the line won't be as difficult as the crib transition.

We pretty much did it cold turkey. I remember it because it was New Year's Eve and our son was about 8 weeks old. We figured it was worth a try and he did totally fine. I wanted to err on the side of doing it early as he'd spend the whole night on the "vibrating" function, and I was worried I'd spoiled him! I say pick a weekend night (especially if you and your husband work/one of you isn't still on leave) and go for it.

ETA: our RNP had been in the nursery next to the crib for a while before the transition, but if he'd been in with us still I likely would have had him in the RNP in the nursery for a few nights before the crib.

@LulaBee: we were very successul with the transition at 8 weeks. We also transitioned to a regular halo sleepsack at that time. He slept beautifully for 4 weeks until I returned to work and he got sick at daycare. He is 16 weeks now and we have him back in the RNP because he is so congested and coughing (has had rsv and bronchiolitis for 4 weeks). He now wakes up 1-4 times per night. I'm not sure whether to blame it on being so sick or the 4 month sleep regression. I hope it goes well for you!!

@LulaBee: I'm sure the transition to daycare will be better for you! It's nice that she's a couple weeks older, hopefully that'll make a difference! If she's not too big for it or rolling then I wouldn't worry about switching her immediately