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We did paci weaning first, then big girl bed, but our "big bed" was actually just the same crib converted with the toddler rail, so I think it was a different kind of transition. In your case, I agree with @Truth Bombs. Just wanted to say that we were terrified to lose our girl's good sleep when we paci weaned, but there were literally no issues at all. In a way, it was good to do it later because she was old enough to understand. We told her the "binky fairy" needed to take her binkies away for babies and that she was a big girl now, and I think she totally got it. She left her pacifiers out in a bowl one day and we replaced them with a toy. She slept totally fine that night and ever since. Baby brother arrived a few months later and we were worried about a possible pacifier relapse but she has no interest in them because "they are for babies".

This is a tough one. We weaned DS from his paci at that age almost exactly and I will say being honest did not work for him. He really didn't care about being a big boy and felt he wasn't too old (he pointed to older kids who still had it).

My first instinct was to say that you should do paci first. We had to do a small degree of CIO with paci weaning because he was unable to settle. I think being trapped in his crib worked in our favor. I'm struggling a little though because you have an escape artist so it's not like he's trapped anyways. Based on that, I'm inclined to say do both at the same time and go through a few weeks of potential hell. Ultimately it's going to take a couple of weeks for both adjustments so I almost think it will be less time if you just deal with both at the same time?

@winniebee: Ha, sorry, that does sound pretty harsh. It was about 7 days for DS to finally be cool with going to bed without paci and sleeping to his normal time. A friend just big boy transitioned and she said it was 2 weeks for things to be 100% normal for her son (and he was a rockstar sleeper).

I think you maybe present it as he's getting a big boy bed and big boys don't have pacis. Maybe he'll think of the big boy bed as like a reward for giving up the paci?

Does his crib convert? Is there a possibility of doing all the transition in his current room without disturbing big brother? If you can convert his crib, I'd probably do it all at one time. Convert the crib, take the paci and get him adjusted. Then move him to the other room. Or if the crib doesn't convert, could you do a temporary floor bed in his current room?

Also, FWIW, we ditched the paci at a younger age, but it was considerably easier than what I worked it up to be in my mind. I'm hopeful you experience the same. That it will be mostly a non-event that you overthought.

@winniebee: You'll have to change it to raise the mattress I get it, I'm not sure I'd want to do all the work either. Maybe a floor bed? Use his new big bed mattress on his current floor?

The thought of my two kids in a room together absolutely terrifies me with the non-sleeping shenanigans. So I was trying to find a way to protect T from the changes.

I'd probably just do it all at once right now. That way hopefully everything is a-ok and he is back to sleeping fine once 3.0 gets here in the summer.

I was going to suggest maybe just doing big bed now, and then paci once 3.0 arrives ("babies are the only ones who get pacifiers! you're a big kid!") but having two potentially bad sleepers at the same time would be ick. So I guess you'd have to be ok with pacifier until some number of months AFTER 3.0 is born then....

I think we did bed then paci but it was back to back. Bed was nbd. Paci was pretty terrible.

We did all at once on his third birthday. It was totally painfree and there was never any confusion about which pacifier is which. Same thing with DD (a month younger than your DS2) she knows which pacifiers are hers and which ones belong to the twins.