I've raised hunting dogs for years, had them die young and unexpectedly, had them die old & of natural causes, but having to make the decision to put down a loyal old dog is always the toughest. As many have already said, as owners we tend to wait too long, very rarely if ever, does a caring dog owner put a dog down too soon. I can tell you watching them "die on their own" at home or in their kennel in the middle of the night is tougher to live with.
My last one was 14, still in good shape & hunted fine with pups 3 weeks before I put him down, a little thin but mobility was fine. Ended up with a terrible infection that travelled into his eyes and brain and could only be fixed (maybe) with surgery. Gave him one last good week at home & he could hardly eat so finally pulled myself together enough to make the trip. I show up and the receptionist is crying already, and the vet loses it while putting in the needle because my buddy who has been there tons of times for other stuff is wagging his tail.....tough day, but still was the right decision. Still have his sister, and pretty much any day will need to make the trip, I think you need to set a line in the Sand with issues you are willing to deal with, for me it's eating, mobility, and old dog anxiety, once I see one or more of those going downhill I need to get serious.