Thanks for all the responses.
Remainsilly touched on something that I think is definitely clouding my judgment. The first scenario with the wine glasses was done by a friend who has broken many of my things and is... generally clutzy and messy and never offers to replace. I think I am especially annoyed because now I perceive it to be a repeated pattern. She is the type of person who borrows clothes and returns them unwashed.
The second instance was just so unexpected because the guest was a MAN! I didn't expect hair dye!
In any case, I think both of these situations must have been really embarrassing for the guest, so I minimized it to help them save face. In the first, she not only broke her wine glass, but dropped it on mine, and they both smashed shards all over the whole chicken fresh from the oven... At a dinner party with other guests. We all had to eat something else!
There have been a bunch of other instances but
mundodabolsa is right that I should not be treating my items as if they are precious, and they really aren't. In all the other situations, I've always thought "I could have done that, no biggie." whether someone borrowed and dinged my car or spilled wine on the rug. But almost everybody at least apologizes and offers to do something. I don't get upset at all and honestly don't want them to worry about it because I don't think of my home as a precious place but as a place where I can relax.
I am going to move my nice towels to my bathroom though!