And your husband letting the dog out of the crate when he cries is training the dog to cry in order to get what he wants.
Letting the dog out when he is calm and quiet is teaching the dog that calm and quiet gets rewarded.
And as Mike says, it's not age that dictates when the dog "gets it" 100%.
Does the dog "get it" in every room of the house? Does he "get it" in the yard with no distractions? Then it's time to see if he gets it with gradually increasing distractions.
I think that lots of people believe that their dog gets it when what the dog knows is to "sit in the kitchen."
I'd set aside some time and really watch it, maybe part each evening for a couple or three evenings; it's not really a half-hour bullet-point video. It's more like "How to live with and obedience train your dog."
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