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The really good news is that Jake doesn't seem to be painful or in any sort of discomfort.
It's actually pretty common for dogs to lose some nerve function as they age. Sometimes this can look like a dog losing strength in the rear legs, making them fall over often, and some may lose control of their fecal material, so they're dropping feces everywhere.
In Jake's case, I suspect that either the nerves are functioning badly, or it's possible that the muscles in the tail are weaker on the side it leans to. Normally we don't worry about it unless it's compromising the way he defecates or if he becomes painful.
I hope this ehlps.