If you really want to escalate a bad neighbor situation from passive aggressive to potentially violent, shooting his dog is likely the best way to do it. I assume that attempts at direct communication have not been successful. Have you spoken with your attorney to see what civil remedies might be available to you? Sometimes a strongly-worded letter from an attorney can work wonders and is not as costly as replacing the broken windows and repainting the garage door to cover the graffiti.

I have been shooting since I was 8 years old, qualified as a master sharpshooter while a LEO, and still hit the range as much as I can. I would not be able to hit a dog "behind the eye socket but in front of the ear" while being charged.

YMMV.