Can I ask a Rover sitter a specific question before trying to book a specific date?

Of course you can ask pretty much anything you need when it comes to your pet. The dog's profile has a question about its potty training and it is always a good idea to enter that information about pee pads into the Comments section.

Also, it isn't clear if your dog will be boarding at the sitter's home or if you intend to hire a house sitter. Regardless, informing the sitter is something one would do at the M&G, while you go over things, or through messaging. I highly recommend that you have a M&G with the sitter prior to booking. Saves everybody a lot of grief.