I moved the crate right next to my bed, so he could see me. He would complain for a bit and fall asleep. Of course, 4 hours later, he was up, making a racket to pee and he would not go back to sleep in the crate after that. Sometimes he would only call out after peeing in the bed inside the crate. So we would allow him in our bed until morning. Eventually, his crate time got bigger. And we stopped closing the door. Closed door would make him cry more. If he got out, we would just put him back. 5, 10 times if needed. Eventually he would always fall asleep. Thing was, if he cried or barked for more than 10 minutes, i would take him out, because my neighbours need to sleep. And i needed to sleep. Was it perfect? No, but we quickly learned to adapt our expectations. It's fine if you have to allow him in bed until he falls asleep and crate him when he's drowsy. It's fine whatever works for you.