IMO, everyday he sleeps out of the crate is reinforcing that he won't have ever have to. I live in an apt too so I'll share with you some pointers. First, are your neighbors complaining? If not let the dog scream it out until they do. Second, you can try closing the door and throwing treats in there as the door is closing. Keep throwing treats in there with the door closed and then open the door. You can extend the time and the amount of treats if this is working. Another thing you can do is when you feed him, close the door when he is eating.
Now, if you want him to sleep in another area, you can sleep in that area with him for a bit until he is more comfortable by himself. My dog sleeps in the 2nd bedroom and I spent two weeks in there with her until letting her sleep by herself.
Now, if you want him to sleep in another area, you can sleep in that area with him for a bit until he is more comfortable by himself. My dog sleeps in the 2nd bedroom and I spent two weeks in there with her until letting her sleep by herself.