Join Date: May 2016
Location: Naples, Florida
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Photo Submissions 30 Times in 28 Posts
Havanese are prone to being clingy and suffer from separation anxiety if not taught early on that being left alone is not a death sentence. There are ways to ease them into a new reality, but it will take perseverance and consistency. You mentioned your son is disabled, which could make concentrating on a dog with needs such as Jerry's a bigger burden than you may be willing to take on. I think a professional trainer/behaviorist could analyze the situation and point you in the direction you need to go.
I went through the same thing with our first Havanese where she cried and yowled for so long that we wound up putting her in bed with us. I didn't make the same mistake this time with Tux. I put him in a puppy pen right next to the bed where he knew he was safe and ignored his cries. Interestingly his favorite sleeping place now, is under a bench next to our bed on a feather pillow. He can see us, and is fine with that. It also took extra effort letting him learn (gradually) that when we left the house (with him in a bathroom with a gate, his pillow, sheet and hidden treats to find while we are gone), he could live through it. You start out with short periods away (a minute, then 5 minutes, etc. ) and build up to a few hours. Your situation is vastly different due to Jerry's age and lack of proper training, which is why you need advice. I had an Akita who never seemed to mind if I left her alone. She marked the grass outside, but never ever peed indoors.