What do you do when a dog ruins your things?

You're welcome to bring up damages with the owner, especially in the context of letting them know that their dog is really only suited to boarding with around the clock supervision or being left in the care of a travel sitter until he/she is comfortable being crated or can be trusted with more freedom. At this point, both crating him/her or leaving him/her free is dangerous. As you've seen, he/she causes self-harm while crated, and could easily ingest something harmful while out. You can also request that they compensate you, but without an agreement in place ahead of time, they are not legally responsible for any damages. If you carry homeowner's/renter's insurance, it may cover damage to your home and belongings, but you'd have to check your insurer to confirm, as some policies only cover damages related to theft/vandalism. I would also contact Rover support to inform them of the damage. Even if the owner isn't liable to cover the costs of replacement, it's worth letting Rover know in order to establish a history if the owner just takes their requests somewhere else and it happens again.

Depending on your business situation, you may be able to deduct the cost of replacement items on your taxes, but you'd want to consult a professional to make sure you met the qualifications.

I've had something similar happen before, and unfortunately Rover will not cover any damages to your home or property. I had a dog stay with me that went out of it's way to get into my hamper, tear out clothes and then destroy them. She also ripped up two pairs of headphones, none of which were with in her reach as a little puggle. I reported it to Rover, just as a precaution and they basically told me; as sitters we allow these dogs into our homes taking full responsibility for what may or may not happen while they are in our care. Even though we do business through Rover.com we are technically self employed, so that's kind of why they don't cover anything.

Best thing to do is take note/photographs of whatever the damage was and let the owner know. More than likely she is aware of her own dogs behavior and will take responsibility for it. Which would hopefully be some means of reimbursement. If not, as rover customer said "chalk it up to a bad experience and learn from it for future stays". Good luck!