Did anyone else let their toddler “cry it out” when transitioning them to sleep in their own room?

Looking for tips or advice, did anyone ever let their toddler “cry it out” when transitioning them to sleeping in their own room? I have a 2 year old who sleeps in bed with me and I’m pregnant so I really want him sleeping in his room by the time baby comes. He will sometimes sleep in his pack n play in my room, but he just cries all night reaching for me until I put him back in bed with me because he can see me. It’s either put him back in my bed or listen to him cry all night. Should I just try putting him in his room tonight and see how he does? And if he cries should I let him or go get him? (I have a 360 camera in his room so I will be able to see him on my phone) or should I let him fall asleep in my bed then move him to his room? Everyone in my family is saying to put him in his room and let him “cry it out” and that he will eventually get used to it but I have never done the CIO method and would feel terrible to let him cry. Should I sleep in his room with him for the first couple nights? Should I allow him his tablet? Should I make it completely dark or leave a lamp on for him? He’s scared of the dark. I feel so bad because I love cosleeping with him and he sleeps so well in my bed but it’s almost time for him to get used to sleeping in another bed by himself and he just cries in my room🥺

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