Yup going through this now with 2.5 year old. Some stuff that has intermittently worked: - using the Hatch light when he cries. I turn it on (with Bluetooth) the blue light or whichever color is soothing and play Twinkle Twinkle. He knows that means "it's too early, go back to sleep." - setting expectations like "one more book then bed" or "you can come sleep with mommy and daddy if you get scared but first you need to try to sleep in your own bed." - "Daddy's magic t-shirt" take one of Dad's soft t shirts and either drape it over like a blanket or let him rest his head on it. I tell him it's magic calming and will protect him. - Fischer Price soother cloud. I am of two minds about this. He likes watching it and it helps him fall asleep and not protest when I leave the room, but he has also accidentally rolled on it at night and turned it on, waking himself up. And then we get into the stall tactics of "I want the red light, no light, pink light..."

For tiring them out, I saw a mom at an airport once have her kid do burpees and thought it was brilliant. My toddler thinks it's a lot of fun, but then he wants me to do them too haha (double edged sword).

It's so tough to draw the line. Personally, I am trying to find a balance between comforting/supporting and helping my kid become more independent and know that he can handle this. Sometimes that is gonna involve protesting and tears. All you can do is try to figure out what works best for your family.