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Have you tried going to a holistic vet? One who has had the Fear Free training might also help.
Have you tried feeding a small amount of plain canned pumpkin like a tsp. to try to bulk up his stools so the anal glands work better?
I was going to suggest pumpkin in his food also. You might try CBD to help calm him, we used ReLeaf with our last dog in her old age and it helped ease her aches and anxiety, she also got homemade bone broth daily for her joints.
If my dog was suffering so horribly with unresolvable, painful health problems, I would know that it was time to reluctantly say good-bye.
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