I’ll give you my take having raised one bird dog puppy and getting ready to raise a second. So obviously I’m no expert. But other bird dog trainers I look up to gave me the same advice.
Sounds like you’re doing great with your daytime crate training! As for the nighttime crying, I would move his crate into the mudroom or the garage at night. Just get up every 2.5 hours and let him out. He’s gonna bark and scream and cry, but he has to learn that that doesn’t do any good. If you ignore him, he will settle in to a routine and stop doing that if he doesn’t get reinforcement.
But if you get up every time he starts making noise and give him the attention he’s looking for that just reinforces the idea that crying and making noise makes you appear. So inadvertently you can train him to cry at night. As difficult as it can be, it’s better to set the ground rules early that sleeping in the crate at night is his solo time (other than potty breaks, of course).
It’s a necessity for puppies to be extremely adorable……….. otherwise they’d never survive to adulthood lol.
But once you get past this stage and hunting this fall, it’ll all be worth it!