I enjoyed the story. So sorry to hear that Bilbo has seen his last sailing trip. I have really enjoyed seeing pics of him accompanying you on all your sailing trips. I understand, as only another dog lover can, how difficult it is to see your friend of so many years starting to struggle.
I'm reminded of my Lab, Mandy, who was barely four when I got my M15 and passed away 12 years ago at the age of 13. She was a great sailor although she preferred the cabin when things were rough or we were beating, and came out into the cockpit when we ran with the wind. The Monty has a great deck for doggy paws, and the dogs (two other Labs as well) loved it. Now I have corgis and their legs are just a little too short to make them good boat dogs, so I leave them home. Bobbie