I had a family consisting of one huge doe and her triplets--two bucks and their sister -- who used to come around our house on a regular basis. One of the little bucks actually looked in the window one time and watched a football game with me!

She was pretty sharp though and not nearly as "understanding and tolerant" as your buck. She managed to elude me when hunting nearly every time--except once. Just like you though, I couldn't bring myself to shoot "momma."
A friend of mine actually raised a buck who eventually went more and more into becoming a wild deer. He thought this might happen and attached pink streamers from the buck's antlers so that hunters would feel strange shooting him.