When I was selling, I would do insurance if the buyer wanted it. I didn't charge anything beyond the cost of the USPS insurance. Most of the stuff I was selling was really inexpensive, so buying insurance was pointless.
I did insure a few expensive packages. Stuff like a plate I sold for a bit over 600, the buyer was surprised when my first email said I'd pick up the insurance. At the time most ebay sellers were charging a lot for insurance. That only cost me maybe $2 at the time.
A friend of mine had a cylinder phonograph damaged in shipping, and the insurance was awkward. Basically he had to take it to one of the bigger post offices, and show them how it was packed. Then he had to take it to someone who did phonograph repairs, and get a written estimate. Then the seller had to take the written estimate plus some paperwork from the PO here, to their local office to make the claim as they'd only pay the person who paid for the insurance. On the plus side, once the running around and paperwork were done it was paid in full in well under a month. I think a week to the seller, and a week for the sellers check to get to my friend.
All that relies on a cooperative seller though, so it may go differently for someone else.
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