This article is from the Toys FAQ, by email@example.com (Scott Gordon) with numerous contributions by others.
From Eric G. Myers (firstname.lastname@example.org):
"There is some controversy regarding this issue. However, if the
buyer wants to pay for insurance on top of all other agreed
terms of your deal, by all means get the insurance requested.
If you are shipping an item of exceptional value (suggestions have
ranged from 25 dollars on up through 250 as minimum values for
obtaining insurance...a happy medium might be 50-100 dollar
value). Here are some of the controversies. First, insurance
will often only cover the ACTUAL value of an item as opposed to
the PERCEIVED value. What that means is that if you are
shipping the latest, currently shipping but rare Spew figure
(let's say Hamburger Head Angela with Specked Panties), it may
only be worth what you paid for it retail. It doesn't matter that
someone sent you $50 for it. For insurance purposes it will
probably be worth retail price. However, there are some
exceptions. If you have an appraisal of value from some
reputable source, you may be able to get more back on an
insurance claim. This is very difficult with
currently available/shipping figures. No matter the rarity, if
its currently available, its probably valued at retail price. Even
with older figures, sometimes an appraisal is not acknowledged by
insurance. If you have questions, contact your local postmaster.
Second controversy: Insurance may only cover the toy inside the
package and NOT the package itself. Many people collect MOMC
[(see Q2.18)]. However, if the card or bubble is damaged in
shipping and the figure is left intact, insurance may not
reimburse you. Again, check with your local postmaster if you
In short, insurance is a matter of choice. Know what is covered and
then decide for yourself. Remember, if the package you send to
someone else does not arrive or arrives damaged, netiquette states
that the shipper is responsible for making amends."