After my last post, I was able to reach out to Pet Sitters International (PSI) with the guide Kim Fields, Chris Wooten, and I developed to help educate and protect pet sitters.
After reading my "Complicated Contracts of Dog Walkers" post, the PSI president Patti Morgan put me in touch with an expert on insuring pet sitters, Mr. David Pearsall of Business Insurers of the Carolinas. Mr. Pearsall has been working with PSI for a decade to protect pet sitters and pet owners.
He was able to give me some additional insights into these complicated contracts.