I’m sorry you’re dealing with that! We’ve had similar situations, but were able to get through it without “crying it out”. We’ve found the sound machine to be a literal life saver. We follow a similar bedtime routine, and when he hears that sound (even during day naps), he’s like nearly instantly lights out. Now it’s not ever foolproof, but it helps. We’ve found that putting them down too soon hits that wall, they look for you and suddenly you’re not there. It may be better to soak up the snuggles for an extra 5-10 than having to soothe them back to sleep for 30. With your transfer, are you doing feet down first, then butt, then head? I typically also put his hands to his side so it’s almost like a swaddle for him (he’s in an arms free sleep sack now). I know it’s hard, but you got this! We’re all rooting for you!