Now that I'm thinking about these people that self insure, I had another thought. What about liability insurance? We have insurance on our vehicles and home and also an umbrella policy. We live in a 4 season climate. What happens if there is ice and the delivery driver slips and falls on our walkway? I'm assuming initially the company, UPS/Fedex/Amazon (if an actual employee vs contracted worker) covers their medical bills. But I'm assuming the company's insurance is going to come back to us for the liability for not having a safe path for them to access our front door. There is a good possibility depending on the severity of a fall, the driver could become paralyzed. That would wipe out everything most people have. As I'm assuming the folks that have millions upon millions are not choosing to self insure. I'm thinking it's the average upper middle class family whose home is paid off and looking to save a little bit each year.
On a side note, we do immediately do snow/ice removal for the drivers, keep lights on when they deliver at night, etc. But you never know what could happen. In a sue happy world, they could just trip without any obstructions and likely there is a way we were negligent.