Here is my update! I waited until she left and then the actual guest who booked came the day after. I let the guest, who I like, know about it and she felt awful and asked me to handle it directly with her boss. I emailed her boss kindly asking for $100 to fix the nail holes and explained that I was surprised she thought it was O.K. to nail something to someone else’s home. The boss (a woman) immediately called my guest and told her how badly she felt and how angry she was at her husband for doing this. The guest told me she said they were “push pins.” They were NOT push pins. The boss was so embarrased she told my guest that she was going to cancel how own plans to come back to help the guest work for the rest of the month and the guest was fine with that. She told her “I cant’ bare to face her.” O.K., fine with me. She said to the guest she would pay me the $100 through paypal as I requested. But it has been two days since I sent the email and I have no payment and have not heard back from her. I’ll wait another day and follow up with another email. Ultimately, I’ll have to ask my guest to leave early if she doesn’t pay. I’m giving them a huge discount for staying for the month for 3 years in a row. I can make more if I have it rented out on the normal calendar. I’m glad to hear she realizes that this was not a good idea. Thank you all for your thoughts. You helped me with my strategy and my email to the boss.
Photos. Photos. Photos.
Your guest screwed up. Now she’s lying as a CYA move.
One of two things will happen.
She may have a month-long snit.
But my money (having had a history with her) is that the rest of the trip will be pleasant and uneventful.
Time for a mental Marguerita. You’ve done your best; now it’s up to them to behave like adults.
Good decision on your part! I hope you stick with it.
Your regular guest benefited from your good graces all these years and she has the opportunity and obligation to come through in this instance where her boss(‘s husband) caused damage. She brought them on board to your rental on her ticket and she should accept all responsibility for their behavior. Your discounted rental terms were with your primary guest and she actually overstepped her bounds by inviting her boss to utilize your rental under the same terms.
The “right” thing for your guest to do is to take care of the damage charge herself so that you are made whole and to deal with her boss on her own. It is your guest who should feel mortified about her boss’s stay and rush to take care of it.
Unless your guest or her boss coughs up the $100 within the next couple of days, I would cut her stay short as soon as possible, giving her a day’s notice. Her inaction would prove she has no moral compass and the relationship is ruined at that point anyway. Since renting to her is less than profitable for you, cut your losses.
Sandy, I couldn’t agree more with your very succinct dissection of the issue and how to solve it.
Hopefully, you have a deposit, which I am sure Airbnb would reward you. I would charge $200 if the repairs are $100 and the rest would be for the hastle and mental stress this has caused you plus mileage and time spent to go to Home Depot for supplies for repairs and your time to procure the supplies and then you time to fix the damage or to find some one to make the repairs and pay him. Also please request that your “guest” be banned from Airbnb for defacing rentals. I don’t want him in my place!
Sandy is soooo articulate!
I was going to reply but I’m at a loss for words ~ thanks! 
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It came at a good time cuz’ I was feeling kinda mopey today…but not any more!!
A guest of mine complained about everything including my house rules. I one, “Common Sense!”