Well let me say first that he will not get over the crying at night with age as long as you are still letting him sleep in your bed. We made that mistake with Caney -- let her sleep with the humans the first two nights, then it was off to the crate (though it was only right next to the bed). She cried and CRIED through the night for 2, maybe 3 weeks. She knew the comfort of the bed and didn't want anything less. I'm afraid the more you let him sleep with you, the worse time he will have adjusting to the crate. As it is, being that he's already been sleeping with you, it's probably going to take a few weeks

But you just have to power through it. I wore earplugs during that time but they still didn't drown out her pitiful cries. BF was about to toss puppy out the window (not really

) and both of us were exhausted for those few weeks from getting no sleep.
I think the biggest reason for leaving a puppy with its littermates for longer is so that they learn how to socialize with other dogs. So, that would be my biggest recommendation -- to find friends with
friendly dogs and puppies and set up play-dates with them so that he can interact with other canines. If he doesn't get that socialization he's more likely to be shy or even aggressive towards other dogs when he's an adult.