I am expanding my pet sitting business and I am wondering about getting town licensing, is it necessary if all my business is done through Rover.com? Does anyone have experience with this?

How you get your business really has nothing to do with it. From the Rover FAQ:

Rover requires that you follow your local laws and regulations regarding licensing and other requirements. Requirements vary by location, so check with your local Animal Control to learn about the regulations where you live.

Often, licensing regulations apply only to facilities that handle a high volume of dogs. If you sit for one or two dogs at a time, you may not need a license. Nevertheless, it’s a good idea to check your local regulations.

It depends on where you live. For instance, I live in the Seattle area. I called the Department of Revenue and told them what I was doing with Rover. Since I currently don't meet any of the six criteria for a business license, I don't need to be licensed with the state; however, the town I live in just outside Seattle requires a business license, no matter what kind of business you're conducting. It is only like, $30. Anyway, start with your state's Department of Revenue, search for business license, see if you meet the criteria in a state level. Then, Google your town's name, look up the criteria for business licenses there. Either email or call them with your questions. 😊 Keep in mind, some towns may require a pet sitting license, too, if you plan on watching more than four dogs at the same time. Ask them about that, too.