My dog-sitter let my dog damage my home - how would you react?

you should submit a claim under the Rover Guarantee program, but I wouldn't hold my breath they will compensate you. Look at Covered Section 4Losses for Damage to Pet Owner Property. https://www.rover.com/tos/guarantee/

This is a difficult one. Dogs will react differently to new people. But again you did tell her to crate the dog. She should be reprimanded in some way. I think I would either deduct part of her fee or make her pay half the repair.

See what Rover recommends.

Always make sure to call Rover because they will try to resolve any issue.