There are so many must-have items for walks so I'm going to cheat on this question and say my backpack in it I have an extra leash and harness, 2 slip leads, dog food, dog treats, water for me, snacks for me water for dogs, a folding bowl, poop bags, a Bluetooth speaker, rain jacket (for those Seattle days) and a multi tool.
For boarding, every sitter should have a baby or pet gate...even if it's the most basic movable type and not something they usually use. When something needs to be cleaned up and paws need to keep away (such as if a food container, especially glass breaks in the kitchen), general cleaning of floors, or temporary separation as needed between pups and bowls at meal time, etc.
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