James,
sad time for you and your family. James looks like a great cat. I'm afraid I can't advise on when is the right time to euthanize. We usually wait perhaps too long. When we were losing our 8-year-old Rottie girl a year ago -- she was in renal failure -- we made the decision before she went into shock and her systems shut down. She was being hydrated with 4 bags of IV fluid a day but she was still there. She had cleaned Cassidy's first litter and had gotten through the Xmas Holidays with lots of company and lots of love. So we said "goodbye" when she was still our Coco.
To me it's always an issue of quality of life. If the animal is all there mentally and is not in pain, then you can put up with a little inconvenience to keep them in your life.
Good luck with your decisions. And good luck to James. May he live a good life for as long as possible.
Jim