I also have a puppy (Izzy is 5 months now) and after reading every single post on puppies/potty training I realized how different our babies can be. Izzy has a very strict routine when I brought her home and still we had many accidents with her. We were lucky that Izzy would sleep through the night and it never crossed my mind to wake up in the middle of the night to take her potty. I just made sure she was taken out around 9pm and we also took her water bowl at 7pm. She would be fine until 6am the next day when I wake up to let her out. Let me know how your puppy is.
Izzy cried the first night in her crate, maybe for 1 hour then she felt asleep. I never had a problem with her and the crate. How's your baby doing? I think that if you create a very positive safe place for him he will love his little cave! I also cover her crate with a towel so it's a little dark in there and she feels safer! Maybe that helped?!
Your baby is adorable and we will enjoy exchanging experiences here and learning from each other!