"And I'm afraid to have him anesthetized. I'm afraid something will happen."
Hey, something did happen. This tooth lost its attachments and was hanging by a thread, which makes it wiggle around and hurt. It wasn't much trouble to extract this one. The tooth ought to be the color of those two white roots, not covered wtih brown crud. That pink dot was the only remaining attachment. The teeth he has left are similarly encrusted with tartar. Some of them are probably in about the same shape, but the tartar is bridging them to the next tooth so they don't wiggle so much.
Now that I've flipped this one out of the poor dog's mouth, they are going to have another family talk about getting his mouth situation handled. [Six months ago, I didn't convince them.]