I think he is starting to get it.
A couple of new developments this week. Very impressive if I'm not reading too much into it.
1. My wife puts her purse on the bed, the pup goes into the crate and lays down.
2. My wife sits on the edge of the couch in our bedroom to put on her shoes, pup goes in the crate and lays down.
3. When I leave for work in the morning my wife has been holding his collar so he doesn't follow me out. He will paw at the gate wanting to go with me to work. This morning when I was leaving he sat down on the other side of the door and she didn't have to hold his collar.
Interesting stuff. He is starting to do it on his own.