I've shipped items worth up to $60,000. Here is my experience:
* I am insured for shipping through Collectibles Insurance. I only purchase postal insurance to cover the $200 deductible. This keeps shipping rates down and I can pass the savings onto my clients.
* For high value items, I use USPS Registered Mail. It may move slowly, but it is the safest and least expensive option for high value items. For instance, $30,000 worth of insurance on a recent item only cost around $55.
* DO NOT use FedEx for anything worth over $1,000. FedEx will take your money for the insurance without question, but if you ever need to file a claim for a "collectible," they will tell you the limit on collectibles is $1,000.
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