I agree with Mrs. K that you already know the answer even if you dont want to admit it. Better a day too soon than a day too late.
Sounds like your guy has had a good long life filled with love but the amount of pain he's in and the amount of assistance he needs is frustrating him and then sedating him only adds to the frustration. Ask your dog. They do tell us when they're ready to go.
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Shasta GSD 5/5/10 CGC, ITD, TC
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Riley GSD/BC 1/10/05-2/1/2013