Thank you. I'll be happy to give you as much info as possible. Yes, he is crated because he has peed on rugs overnight. We normally crate them around 11:30, and he has normally been asleeep for at least two hours. He can go outside any time up to the time of creating, but he rarely asks to go out past 9pm. We have tried to make him go out later, and he just won't get up. We have not tried offering a treat to go out.
His last meal is at 6pm. We have tried giving him 3 meals so the last one is around 9, but it hasn't affected the barking. He does not have toys in the crate. He does love bones, so maybe that would be good.
The walking is a problem. They have a fenced area to run around in, but they don't get consistent walks. Especially now, because I have my foot in an aircast. I'm seeing from your questions, that this might have something to do with the problem!
It is amazing! We are now taking the dogs on a quick walk at 10, giving them chew toys in the kennel, and the barking has stopped. He was just bored and not tired enough to sleep. Thank you so much!