Should Painter Have Insurance?

Yes.

Painters must have several types of insurance: business/liability insurance and worker's compensation. The business/liability insurance covers the painter for any incidental problems, such as a ladder falling and breaking something expensive in your home. You'll want this coverage because if the painter isn't covered and something happens, then you have recourse. Without insurance, you are on your own.

The second type of insurance is worker's compensation. This is required by law (may depend on your state) and covers any work-related injury. If your painter doesn't have worker's compensation and someone gets hurt while working on your home, guess who is responsible for the medical bills... you. So this is also really important.

If the painter doesn't have insurance, guess who becomes the insurer? Insurance companies get paid a lot of money to provide the level of insurance they do. Why should you assume this risk for free?

Insist on seeing proof of insurance.