Just saw this, and thought I'd put my perspective in because I was unable to use a gate with two of them in there to entertain each other. The girls were vaulting out of their cribs and after several options that failed miserably we put their crib mattresses on the floor.
We did our transition almost 8 weeks ago. It took 6.5 of those weeks for me to get to the point of them going to sleep within 20 mins with me still in the room. I knew it would be hard with D particularly as she doesn't travel well and they both need their routines so badly. This is how the first 6 weeks or so went:
Weeks 1 and 2 - both girls screaming for their cribs for hours on end and only going to sleep if they were physically touching me.
Weeks 3 to 6 - different variations of wi/wo which also failed miserably. I did my best to be consistent with everything but with the two of them and the vast space of freedom, they were just unable to function without more guidance. I had a rocking chair in the hallway and could see them from the crack through the door without them seeing me but there was just too much freedom for them to functionally go to sleep.
Week 7 - I switched to gradual withdrawl and had success literally within 15 minutes. I moved a single bed in between their mattresses and that's where I hang out while they drift off or in early mornings until the timer on their lamp comes on. J gets a 30 second back rub, kiss and hug and she is now putting herself to sleep within 15 minutes. D is a little more challenging and needs a hand still on her after her back rub until she's quite drowsy and then drifts off. We put a rail on D's mattress to give her that 'closed in' feeling again and it seems to have really helped.
We're also dealing with molars, separation anxiety that kicks in with the hysterical 4am - 5am EW's which is why I keep my bed in there. They're not allowed into the bed with me until the light goes on at 7am but they know I'm there and I'm noticing the EW's are moving closer to 6am/6:30am. We ditched their nap due to them going to bed at 6:15pm, asleep by 6:30pm and usually out for 13 hours on a good night. We do a quiet time after lunch where sometimes they doze but usually we just cuddle and watch tv on really low. They were really young to get rid of the nap and I wouldn't recommend it unless you were getting what you feel your lo needs in the night without being tired/cranky more than normal come supper time.
I know that because they're twins the dynamic was different for us, but since they're so close in age to your lo I wonder what developmentally may be causing your challenges with nap/bedtime. I'm also pregnant and desparately craving sleep, and I understand that it's not easy to sit and cuddle your lo at this point in your pg.
Just thought I'd share my experience. We're not up to wi/wo yet but it's coming hopefully soon. I don't mind the 15 mins - 1/2 hour it takes to be in there because it's so much better than 2-3 hours of screaming and frustration. Although children can have a temperment, sometimes developmental issues can throw a wrench into all of the best plans and advice in the world. How to adapt is the most entertaining challenge sometimes
Big Big hugs to you and your family
I hear stories about easy transitions to big beds and I'm so envious. I hope this helps.
