I insure the item for replacement value. Even if I ship a 2009 Easton Reveal that I paid the guy to take, I insure it for $300. I've never had an issue, and I think it's because I have it insured.
Sad to say, but hundreds of bats are lost every year, which is amazing, because when I worked in small package shipping for 7 years shipping dozens of items a day we lost one package, and had two damaged, so how bats get lost more than every other item in the world is beyond me. I'd bet 99% are not insured, and then it's the poor me, I don't have $200 just sitting around to pay the buyer back.
Insure your stuff, unless you keep the funds in your PayPal available for the loss of the item.