My heart breaks for you! Last summer I had to put down my 12yr old malmute\shephard cross. Is was the hardest thing to do but I knew it was best for him. He has a basketball size tumour on his side. He wasn't in pain but he lost ALOT of weight and would vomit when he ate. I knew his quality of life was not very good and that it was time to let hime go. I miss him everyday but I know it was best for him.
Hope this helps alittle and remember that he gave you so many years of love and happiness it is up to you to give him his peace.