What I tell my puppy owners is that if the puppy will be crated during the day, then it SHOULD sleep with them at night. What is the sense of having a companion that is in a crate during the day, and in the crate at night?
I had Caesar crated during the day while I was at work and at night because I had Beta who was the same age, but completely an out of control basenji due to her rescue background. They were crated together. Neither ever complained.
Caesar complained as a puppy.
Each situation is different and unique I suppose.