We always ask the following because they are deal breakers for us .
For Dogs - where are they walked ? If the sitter is required to transport them daily our car to get to that location it’s a decline from us
Where do the pets sleep ?
Are all the pets registered with a vet and is an account set up for payment ? Read this thread for the reasoning behind this question Sitter has to pay veterinary expenses up front!
What are the date and time you are leaving / returning ?
This has frequently led to surprising answers - very often hosts are leaving or returning a day later or earlier than the listing . So this question helps avoid any last minute surprises. There was also a 12 day listing where the hosts built in overlap either end so they were only away for 7 days - we withdrew our application after that call ..