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I've been thru this so many times and it's never gotten any easier. The anniversary will come up this Monday of when I had to do it with my last dog, Brigitte. She had congestive heart failure and her kidneys shut down. God love her, she tried, she had an incredible will to live, but it wasn't to be.
The tears in my eyes are not only for her, but for you as well. I've had lots of dog family and miss them all. My heart goes out to you.
As trite as it sounds, your boy led an incredibly wonderful and long life with a loving family. He couldn't have wanted more.