I would be hesitant to self-insure for liability. The mere condition that one qualifies to self-insure implies that they have significant assets. An injured party seeking damages may seek to expose those assets and make extensive claims against them. With a conventional auto insurance policy an injured party can still seek damages exceeding the the limits of the insureds policy, but they are not as likely to do so because the insured typically has limited assets. As your potentially vulnerable assets increase you can generally reduce the risk of someone taking the trouble to pursue them by simply raising the limits of your policy in line with those assets for a few extra $ per term. It might also help to hide assets from potential forfeiture (i.e., have assets other than real property and documented financial accounts). The bottom line comes down to how expensive could an improbable claim against you be, and how much are you willing to pay out of pocket for the damages.