Should a sitter have insurance before sitting?

I do not have insurance outside of what Rover covers.

I think that's one of the neat things about using Rover, since it's expected that 'regular' people will want to become great sitters without the extra hassle of becoming their own business or service.

Just remember to make sure to book on the site... I've had multiple people ask me if they can get a discount for paying cash directly, and I have to decline. I just am not comfortable without the insurance and customer service Rover provides!

Rover provides insurance to cover the visits, so I don't think you need any additional insurance. I don't.

It depends on what you are doing and how much protection you want. In all honesty, any time we take an animal under our care, we accept the risk that if something catastrophic were to happen, the owners could sue us. The Rover insurance would not protect us from anything like that. If you want to be protected in that situation, set up an LLC or corporation, business licensing, and liability insurance. Now, how likely is that to happen? Probably not very, but it is an outside possibility.